Acetyl chloride → HCID 86585080, compound

HRID 1264429Notes

Reaction equation

HRID 1264429 reaction equation
[SH:1][C@H:2]1[CH2:6][N:5]([S:7]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)(=[O:9])=[O:8])[C@H:4]([C:20]([N:22]([CH2:31][C:32]([OH:34])=[O:33])[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:21])[CH2:3]1.[C:35](Cl)(=[O:37])[CH3:36]>N1C=CC=CC=1>[C:35]([S:1][C@H:2]1[CH2:6][N:5]([S:7]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)(=[O:9])=[O:8])[C@H:4]([C:20]([N:22]([CH2:31][C:32]([OH:34])=[O:33])[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:21])[CH2:3]1)(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86585049HCID 86585049, compound

Product 1

HCID 86585080HCID 86585080, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 124 mg (0.2 mmol) (2S,4R)-{[4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-phenethyl-amino}-acetic acid in 3.2 ml pyridine were treated at 0° C. with 0.04 ml (0.4 mmol) acetyl chloride and stirred for 10 min at RT. The reaction was poured on ice water and extracted wit 1N HCl/EtOAc (3×). The organic phases were washed with aqueous 1 N HCl and 10% NaCl, dried over Na2SO4 and evaporated. Precipitation from CH2Cl2/Pentane (4° C.) gave 30 mg (28%) (2S,4R)-{[4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-phenethyl-amino}-acetic acid, mp: 190-193° C.; MS: 539 (M-H)−.

Workup

  1. additionThe reaction was poured on ice water
  2. extractionextracted wit 1N HCl/EtOAc (3×)
  3. washThe organic phases were washed with aqueous 1 N HCl and 10% NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customPrecipitation from CH2Cl2/Pentane (4° C.)

Sources & evidence

ORD record
ord-06f780d1816842a8b3c8f699786e8711
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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