N-(tert-Butoxycarbonyl)glycylglycine
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N-(tert-Butoxycarbonyl)glycylglycine
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CAS No:
31972-52-8
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Formula:
C9H16N2O5
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Chemical Name:
N-(tert-Butoxycarbonyl)glycylglycine
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Synonyms:
BOC-L-GLYCYL GLYCINE;BOC-GLY-GLY-OH;(2-TERT-BUTOXYCARBONYLAMINO-ACETYLAMINO)-ACETIC ACID;N-(2-N-BOC-AMINO-ACETYL)-GLYCINE;BOC-GLYCYLGLYCINE;N-(tert-Butoxycarbonyl)glycylglycine;2-(2-(tert-butoxycarbonylamino)acetamido)aceticacid;Boc-Glycine-Glycine
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CAS No:
N-(tert-Butoxycarbonyl)glycylglycine Basic Attributes
232.23
232.105927
1533716-785-6
334375
DTXSID40318732
2924199090
Characteristics
105
-0.1
White Powder
1.2±0.1 g/cm3
132 °C
488°C at 760 mmHg
249.0±24.6 °C
1.483
-15°C
N-(tert-Butoxycarbonyl)glycylglycine Use and Manufacturing
General procedure: Amino acid or peptide (1 mmol) was added with stirring to a solution of guanidine hydrochloride (15 molpercent) and di-tert-butyl dicarbonate (2.5-3 mmol) in EtOH (1 mL), at 35-40°C. The reaction mixture was continued to stir until a clear solution was obtained. EtOH was evaporated under vacuum and the residue was successively washed with water (2 mL) and hexane or petroleum ether (2 mL) to afford almost pure N-Boc amino acids or N-Boc peptides. If necessary, the crude products could be recrystallized for further purification.Et3N (3.16 mL, 22.71 mmol) and Boc2O (3.63 g, 16.65 mmol) wereadded to a suspension of diglycine (7; 2.00 g, 15.14 mmol) in a mixtureof dioxane (60 mL) and H2O (10 mL) at 0 °C. The mixture wasstirred at 23 °C for 16 h, diluted with H2O (250 mL), and acidifiedto pH 3 by addition of solid KHSO4. The mixture was extracted withEtOAc (5 × 50 mL), the combined organic phases were dried(Na2SO4), and all solvents were removed under reduced pressure;this gave 8 as a white solid, which was used without further purification.Yield: 3.10 g (13.35 mmol, 88percent).1H NMR (400 MHz, DMSO): δ = 12.55 (br s, 1 H), 8.03 (t, J = 5.5Hz, 1 H), 6.96 (t, J = 5.7 Hz, 1 H), 3.75 (d, J = 5.7 Hz, 2 H), 3.56 (d, J = 5.8 Hz, 2 H), 1.37 (s, 9 H).Triethylamine (Et3N)(3.16 mL, 22.71 mmol) and Boc2O (3.63 g, 16.65 mmol)were added to a suspension of diglycine (2.00 g, 15.14 mmol) in a mixture of dioxane (60 mL) and H2O(10 mL) at 0 C. The reaction mixture was maintained withstirring at 23 C for 16 h. Then, H2O (250 mL) was added, and the reaction mixture was acidified to pH 3 by the additionof solid KHSO4. The product was extracted with ethylacetate (5 × 50 mL), and residual water in the organicphases was removed with Na2SO4. Finally, all solventswere removed using a rotary evaporator to yield product6 as a white solid without purification. Yield: 3.10 g (88percent).1H NMR (300 MHz, DMSO‑d6) 12.6 (s, 1H), 8.0 (t, 1H, J = 5.8 Hz), 7.0 (t, 1H, J = 6.0 Hz), 3.8 (d, 2H, J = 5.8 Hz), 3.7 (d, 2H, J = 6.1 Hz), 1.4 (s, 9H). 13C NMR(125 MHz, DMSO‑d6) 174.6, 171.0, 156.2, 79.5, 44.6, 42.6, 28.4. ESI-MS (m/z) calcd. For C9H16N2O5: 232.1;233.004 [M + H]+. Elemental analysis: calculated forC9H16N2O5: C 46.6, H 6.9, N 12.1. Found: C 46.5, H 7.3, N 12.1.
Computed Properties
Molecular Weight:232.23
XLogP3:-0.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:232.10592162
Monoisotopic Mass:232.10592162
Topological Polar Surface Area:105
Heavy Atom Count:16
Complexity:282
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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N-(tert-Butoxycarbonyl)glycylglycine
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