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BOC-L-glutamine

BOC-L-glutamine structure

CAS No:
13726-85-7
Formula:
C10H18N2O5
Chemical Name:
BOC-L-glutamine
Synonyms:
L-Glutamine,N2-[(1,1-dimethylethoxy)carbonyl]-;Glutamine,N2-carboxy-,N2-tert-butyl ester,L-;Glutamine,N2-carboxy-,N-tert-butyl ester;N2-[(1,1-Dimethylethoxy)carbonyl]-L-glutamine;tert-Butoxycarbonyl-L-glutamine;Nα-tert-Butoxycarbonyl-L-glutamine;N2-tert-Butoxycarbonyl-L-glutamine;N-(tert-Butoxycarbonyl)glutamine;BOC-glutamine;Nα-(tert-Butoxycarbonyl)glutamine;N-(tert-Butoxycarbonyl)-L-glutamine;BOC-L-glutamine;NSC 334370;(S)-2-[(tert-Butoxycarbonyl)amino]-4-carbamoylbutanoic acid;(S)-5-Amino-2-[(tert-butoxycarbonyl)amino]-5-oxopentanoic acid;(2S)-5-Amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid;2483-14-9
Categories:
Pharmaceutical Intermediates > Antineoplastics

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Description

White fine crystalline powder

BOC-L-glutamine Basic Attributes

Molecular Weight：

246.26

Exact Mass：

246.26

BRN：

2127805

EC Number：

237-296-8

HScode：

29241990

Characteristics

PSA：

119

XLogP3：

-0.2

Density：

1.2430 (rough estimate)

Melting Point：

48.0-49.8 °C

Boiling Point：

389.26°C (rough estimate)

Flash Point：

261.7±28.7 °C

Refractive Index：

-4 ° (C=2, EtOH)

Water Solubility：

Soluble in DMSO and methanol. Soluble in 1 mmole in 2 ml DMF.

Storage Conditions：

−20°C

Specific rotation：

-3.5 º (c=2,C2H5OH)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

safety instructions：

22-24/25

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 4 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

BOC-L-glutamine Use and Manufacturing

Methods of Manufacturing

N (Boc)-L-Glutamine (1): L-Glutamine (25g, 0.l7lmol) (Procured fromSpectrochem chemicals) was dissolved in (300 mL) of aqueous solution of NaOH (21.9, 0.547 mol).The solution was cooled and a solution of Boc anhydride (0.205) in THF (150 mL) was added at <10°C (Exothermic reaction).Then the reaction mixture was stirred at 25°C for 20 h. TLC control: MeOH, CH2C12 (1:1) with 0.1percent AcOH. The organic phase was separated off, the water phase was extracted with hexane (100 mL), and acidified by 2N HCLto pH 2, and extracted with ethyl acetate (2x250 mE). Combined organic phase was dried over Na2SO4, then evaporated by vacuum, diluted with methylene chloride, and evaporated again. The product is obtained as a sticky oil, which could be crystallized by hexanc to after standing for 2-3 days to yield N-(Boc)-L-glutamine (1) (37.5g, 89percent)as colorless solid.1H NMR (DMSO, 300 MHz) 7.27 (111, s, OH), 6.97 (2H, d, J=7.92Hz, NH), 3.83 (1H, m, J=4.29 Hz, H-3), 2.09 (211, t, J=9.54 Hz, H-5), 1.9082-1.6856 (2H, m, H-4), 1.3687 (9H, s, H-6) ESI-MS (m/z):269(M+Na)Glutamine 2KG, 10percent sodium carbonate solution 40 liters, stirred to dissolve, add acetone 20 liters, and then at room temperature was added dropwise a mixture of di-tert-butyl dicarbonate 5KG and 4 liters of acetone, while constantly adjusted with sodium carbonate PH = 8 -9, at room temperature overnight.The mixture was adjusted to pH 2 with 3N hydrochloric acid and extracted five times with ethyl acetate. The combined ethyl acetate was washed three times with saturated brine and the ethyl acetate was distilled off to obtain 1.3 kg of tert-butoxycarbonyl-L-glutamine.

Uses

Protected Glutamine.

Manufacturing Info：

L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]-: INACTIVE

Computed Properties

Molecular Weight:246.26
XLogP3:-0.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:246.12157168
Monoisotopic Mass:246.12157168
Topological Polar Surface Area:119
Heavy Atom Count:17
Complexity:308
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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