Triethylamine → 1,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

HRID 2256379Notes

Reaction equation

HRID 2256379 reaction equation
Cl.NCCS.C(N(CC)CC)C.[C:13]([NH:20][C@H:21]([CH:23]=[O:24])[CH3:22])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>CN(C)C=O>[C:13]([NH:20][C@H:21]([CH2:23][OH:24])[CH3:22])([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9082Cysteamine HydrochlorideHCID 7015728tert-butyl N-((2S)-1-oxopropan-2-yl)carbamate

Product 1

HCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6.82 g (60 mmoles) of cysteamine hydrochloride is dissolved in 50 ml of dimethylformamide, and the solution is neutralized with 8.4 ml of triethylamine. The solution is mixed with a solution of crude Boc-L-alaninal obtained by oxidizing 8.75 g (50 mmoles) of Boc-alaninol in 50 ml of dimethylformamide, and mixture is stirred overnight at room temperature. The solvent is distilled off under reduced pressure, the formed crystals are dissolved in ethyl acetate, the solution is washed with 10% citric acid and saturated aqueous sodium bicarbonate, and the ethyl acetate layer is dried. The solvent is distilled off under reduced pressure to obtain 4.93 g (42.6%) of the desired compound 9-A as white crystals. Melting point 81.0°-84.1° C. MS 232 (M+), 159 1H-NMR (CDCl3, δ) 1.24(3 H, d, J=6.6 Hz), 1.45(9 H, s), 2.1(1 H, br), 4.42(1 H, d, J=8.1 Hz)

Sources & evidence

ORD record
ord-5c4fcaf690974e7fbc559c75835f8858
Source dataset
uspto-grants-1997_08
Patent number
US05654399

Reaction notes

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