Triethylamine → ((2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-carbamic acid benzyl ester

HRID 852572Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@H:9]([OH:12])[CH2:10][NH2:11])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.Cl[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>CN(C=O)C>[CH2:32]([O:31][C:29](=[O:30])[NH:11][CH2:10][C@@H:9]([OH:12])[C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:20])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ((1S,2R)-3-amino-1-benzyl-2-hydroxy-propyl)-carbamic acid tert-butyl ester (D102) (25.6 g, 91.4 mmol, 1 equiv) in DMF (250 ml) at 0° C. was treated with NEt3 (15 ml, 108 mmol, 1.2 equiv) and then with benzyl chloroformate (14 ml, 98 mmol, 1.1 equiv) in DMF (50 ml) dropwise. The resulting solution was stirred at 0° C. for 1 h and at room temperature for 16 h and then concentrated in vacuo. The residue was partitioned between AcOEt and saturated aqueous NaHCO3 solution. The resulting precipitate was diluted with H2O and filtered to give ((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-carbamic acid benzyl ester (D103) (31.5 g, 83%) as a white solid.

Workup

concentrationconcentrated in vacuo
customThe residue was partitioned between AcOEt and saturated aqueous NaHCO3 solution
additionThe resulting precipitate was diluted with H2O
filtrationfiltered

Sources & evidence

ORD record: ord-6be70615fe1d48f89146a638d45833be
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253198B2

Reaction notes

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