Dimethyl Sulfoxide → (1S)-[1-(2-oxo-propylcarbamoyl)-ethyl]-carbamic acid tertbutyl ester

HRID 1432902Notes

Reaction equation

HRID 1432902 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16](=[O:27])[NH:17][C@H:18]([C:20](=[O:26])[NH:21][CH2:22][CH:23]([OH:25])[CH3:24])[CH3:19])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[C:11]([O:15][C:16](=[O:27])[NH:17][C@H:18]([C:20](=[O:26])[NH:21][CH2:22][C:23](=[O:25])[CH3:24])[CH3:19])([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86592543(2RS, 1S)-[1-(2-hydroxy-propylcarbamyl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 53756530(1S)-[1-(2-oxo-propylcarbamoyl)-ethyl]-carbamic acid tertbutyl esterYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethylsulfoxide (7.16 ml, 100.8 mmol) is added to a solution of oxalyl chloride (4.41 ml, 50.4 mmol) in 126 mL of methylene chloride at −78° C. The mixture is left to stir for fifteen minutes, and a solution of (2RS, 1S)-[1-(2-hydroxy-propylcarbamyl)-ethyl]-carbamic acid tert-butyl ester (9.92 g, 40.32 mmol) in 100 mL of CH2Cl2 is added dropwise. After stirring for 15 minutes at −78° C., the reaction is quenched with triethylamine (28 mL, 381 mmol), and the temperature is allowed to rise to room temperature. The volatile solvents are removed, and the residue is purified by flash column (SiO2, 60% EtOAc/Hexane). The product (1S)-[1-(2-oxo-propylcarbamoyl)-ethyl]-carbamic acid tertbutyl ester (5.93 g, 60%) is isolated as a white solid. MS C11H20N2O4 MS m/z: 245.

Workup

  1. waitThe mixture is left
  2. stirringAfter stirring for 15 minutes at −78° C.
  3. customto rise to room temperature
  4. customThe volatile solvents are removed
  5. customthe residue is purified by flash column (SiO2, 60% EtOAc/Hexane)

Sources & evidence

ORD record
ord-da0b6fa484f24803a70674363067fc58
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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