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

HRID 852572
Notes
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Reaction equation

HRID 852572 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 10333883tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamate

Product 1

HCID 21356811((2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-carbamic acid benzyl esterYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

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

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between AcOEt and saturated aqueous NaHCO3 solution
  3. additionThe resulting precipitate was diluted with H2O
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes