Water → HCID 59185401, compound

HRID 655108Notes

Reaction equation

HRID 655108 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][C@@H:8]([CH3:11])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].[C:13](Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].CCN(CC)CC.O>C(Cl)Cl>[C:13]([O:10][CH2:9][C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:12])[CH3:11])(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Product 1

HCID 59185401HCID 59185401, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the commercially available tert-butyl[(1S)-2-hydroxy-1-methylethyl]carbamate (1.0 eq.) in DCM (0.19M), pivaloyl chloride (1.1 eq.) and Et3N (1.1 eq.) were added. The reaction mixture was stirred at RT for 48 h, then water was added and the organic phase was separated and washed with 10% aqueous citric acid. The residue was purified by column chromatography on silica gel eluting with 92:8 PE/EtOAc.

Workup

  1. customthe organic phase was separated
  2. washwashed with 10% aqueous citric acid
  3. customThe residue was purified by column chromatography on silica gel eluting with 92:8 PE/EtOAc

Sources & evidence

ORD record
ord-922cb2edb72b4d0c9d9b8d6913ed98cd
Source dataset
uspto-grants-2011_12
Patent number
US08071568B2

Reaction notes

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