Dimethyl Sulfoxide → Benzyl [(1S)-3-oxo-1-phenylpropyl]carbamate

HRID 2102880Notes

Reaction equation

HRID 2102880 reaction equation
CS(C)=O.[OH:5][CH2:6][CH2:7][C@H:8]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl.C1(C)C=CC=CC=1>[O:5]=[CH:6][CH2:7][C@H:8]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 11550966HCID 11550966, compound

Product 1

HCID 59710465Benzyl [(1S)-3-oxo-1-phenylpropyl]carbamate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Sulphur trioxide pyridine complex (965 g, 6.1 mol) was slurried in dichloromethane (2 l) under an atmosphere of nitrogen. Dimethylsulfoxide (2 l) was added and the resultant solution was cooled to 0° C. A solution of benzyl (1S)-3-hydroxy-1-phenylpropylcarbamate (577 g, 2.0 mol), triethylamine (845 ml, 6.1 mol) and dimethylsulfoxide (1 l) in dichloromethane (1 ml) was added slowly to the reaction mixture keeping temperature below 10° C. The resultant yellow solution was stirred at 0° C. for 2.5 hours. A sample was analysed by TLC indicating that all starting material was consumed. Water (8.6 l) was added and a biphasic mixture was obtained. The mixture was diluted with toluene (8.6 l) and the layers were separated. The organic layer was concentrated under reduced pressure to yield a brown foam, which was taken on to Preparation 19 without further purification.

Workup

  1. customtemperature below 10° C
  2. customwas consumed
  3. additionWater (8.6 l) was added
  4. customa biphasic mixture was obtained
  5. customthe layers were separated
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customto yield a brown foam, which
  8. customwas taken on to Preparation 19 without further purification

Sources & evidence

ORD record
ord-52a7d2a8cc144b87ad592aab858e4a7d
Source dataset
uspto-grants-2009_08
Patent number
US07576097B2

Reaction notes

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