Methyl (2S)-4-(methylsulfinyl)-2-[[(phenylmethoxy)carbonyl]amino]butanoate → Z-L-a-vinyl-Gly-OMe

HRID 58389Notes

Reaction equation

HRID 58389 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:5][CH2:6]S(C)=O>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[CH:5]=[CH2:6]

Participants

3

Reactant 1

HCID 11077876Methyl (2S)-4-(methylsulfinyl)-2-[[(phenylmethoxy)carbonyl]amino]butanoate

Product 1

HCID 10922916Z-L-a-vinyl-Gly-OMe

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sulfoxide 60 (5.69 g, 18.2 mmol) was placed in a round bottomed flask in a kugelrohr. This was directly connected to a low vacuum diaphragm pump and heated/distilled at 140° C. The distillate was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether to yield a colourless oil, 0.905 g, 20%. Rf=0.24 (1/7 EtOAc/(50/70) petroleum ether).

Workup

  1. distillationheated/distilled at 140° C
  2. distillationThe distillate was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether
  3. customto yield a colourless oil, 0.905 g, 20%

Sources & evidence

ORD record
ord-4a43dbe2ee32438e853b9f525669c8c8
Source dataset
uspto-grants-2016_09
Patent number
US09434762B2

Reaction notes

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