1-Amino-2-propanol → (2RS, 1S)-[1-(2-hydroxy-propylcarbamyl)-ethyl]-carbamic acid tert-butyl ester

HRID 1432901Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OC(C)C)=O.C1(C)C=CC=CC=1.[NH2:35][CH2:36][CH:37]([OH:39])[CH3:38]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:11](=[O:13])[NH:35][CH2:36][CH:37]([OH:39])[CH3:38])[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

N-(tert-Butoxycarbonyl)-L-alanine (10.0 g, 52.8 mmol) is dissolved in 150 mL of THF. Once the triethylamine (11.0 ml, 79.2 mmol) is added, the solution is cooled to 0° C. Isopropyl chloroformate in toluene (1M) (52.8 ml, 52.8 mmol) is added slowly followed by the addition of (2RS) 1-amino-2-propanol (6.1 ml, 79.2 mmol). After stirring overnight, the mixture is washed with 1N sodium hydroxide and 1N hydrochloric acid. Concentration of the organic solvent afforded (2RS, 1S)-[1-(2-hydroxy-propylcarbamyl)-ethyl]-carbamic acid tert-butyl ester (9.92 g, 76% yield) as a clear oil.

Workup

washthe mixture is washed with 1N sodium hydroxide and 1N hydrochloric acid

Sources & evidence

ORD record: ord-088c6c3755504605a9ca632d0f386bc7
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612075B2

Reaction notes

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