Oxalyl chloride → (RS)-2-[[2-[(Benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride

HRID 275595Notes

Reaction equation

HRID 275595 reaction equation
[CH2:1]([O:8][C:9]([CH:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:12][S:13]([C:16]([CH3:21])([CH3:20])[C:17](O)=[O:18])(=[O:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:32])=O>O1CCCC1>[CH2:1]([O:8][C:9]([CH:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:12][S:13]([C:16]([CH3:21])([CH3:20])[C:17]([Cl:32])=[O:18])(=[O:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 20088400(RS)-2-[[2-[(benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionic acid

Product 1

HCID 20088482(RS)-2-[[2-[(Benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.0 g (2.5 mmol) of (RS)-2-[[2-[(benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionic acid and 1.07 ml (12.5 mmol) of oxalyl chloride in 2 ml of tetrahydrofuran was heated at 500 for 18 hours. Thereafter, the reaction solution was evaporated under reduced pressure. The residue was taken up twice in 30 ml of toluene each time and again evaporated under reduced pressure each time. (RS)-2-[[2-[(Benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride was obtained as a yellowish oil in quantitative yield and was used in the following step without purification and characterization.

Workup

  1. customThereafter, the reaction solution was evaporated under reduced pressure
  2. customagain evaporated under reduced pressure each time

Sources & evidence

ORD record
ord-ed65233ffb6143ccac2acb29d78e9652
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Reaction notes

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