4-Boc-1-piperazineacetic acid
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4-Boc-1-piperazineacetic acid
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CAS No:
156478-71-6
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Formula:
C11H20N2O4
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Chemical Name:
4-Boc-1-piperazineacetic acid
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Synonyms:
BOC-4-CARBOXYMETHYLPIPERAZINE;2-(1-BOC-PIPERAZIN-4-YL)-ACETIC ACID 2 H2O;2-(1-TERT-BUTOXYCARBONYL-PIPERAZIN-4-YL)-ACETIC ACID 2 H2O;1-BOC-4-CARBOXYMETHYL PIPERAZINE;4-[(1,1-DIMETHYLETHOXY)CARBONYL]-1-PIPERAZINEACETIC ACID;[4-(tert-butoxycarbonyl)piperazin-1-yl]acetic acid dihydrate;[4-(tert-butoxycarbonyl)piperazin-1-yl]aceticacid2H2O;2-(1-TERT-BUTOXYCARBONYL-PIPERAZIN-4-YL)-ACETIC ACID 2-HYDRATE
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CAS No:
Safety Information
IRRITANT
NONH for all modes of transport
Xi
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H303 (50%): May be harmful if swallowed [Warning Acute toxicity, oral]|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 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4-Boc-1-piperazineacetic acid Use and Manufacturing
b) 2-(4-(tert-Butoxycarbonyl) piperazin-l-yl) acetic acidTo a solution of the compound of Intermediate Example 23(a) (1.5 g, 5.51 mmol) in methanol (10 ml) was added aqueous solution of NaOH (0.8 g, 22.0 mmol, 4 eq). The mixture was stirred at RT for 2 h. The mixture was concentrated and extracted as in Intermediate Example 5(c). The solvent was distilled off to give the product in 76 percent yield (1 g). LC-MS (ESI): Calculated mass: 244.29; Observed mass: 145.1 [M- Boc+H] To a solution of the compound of Intermediate Example 23(a) (1.5 g, 5.51 mmol) in methanol (10 ml) was added aqueous solution of NaOH (0.8 g, 22.0 mmol, 4 eq). A solution of 4-ethoxycarbonylmethyl-piperazine-l-carboxylic acid tert-butyl ester (1.3 g, 4.78 mmol) in methanol (50 ml) was treated with NaOH (IN, 10 ml, 10 mmol) and stirred for 4 h. The mixture is concentrated and the residue is adjusted to pH 6 with 5percent citric acid solution. The mixture is extracted with ethyl acetate, dried over sodium sulfate and concentrated to give 4-carboxyrnethyl-piperazine-l-carboxylic acid tert-butyl ester, 445 mg (38percent) as a white solid. ESI MS m/z 1179 (M + HIntermediate 27 (a) (3.6 G, 13.2 MMOL) and a 5percent aqueous KOH solution (90 mL, 80.0 MMOL) were stirred in tetrahydrofuran (30 mL, 0.44 M) at 22 °C for 2 hours. The volatiles were removed in vacuo and treatment with strongly acidic DOWEX-50 (WX8-200), elution with ammonium hydroxide (1.0 N), and treatment with AMBERLITET' CG-50 afforded Intermediate 27 (b) (1.2 G) in 37percent yield. APOS;H-NMR (d6-DMSO) : 8 3.35-3. 31 (m, 4H), 3.21 (s, 2H), 2.52-2. 41 (m, 4H), 1.39 (s, 9H).
Computed Properties
Molecular Weight:244.29
XLogP3:-1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:244.14230712
Monoisotopic Mass:244.14230712
Topological Polar Surface Area:70.1
Heavy Atom Count:17
Complexity:290
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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