Acetyl chloride → HCID 10141595, compound

HRID 1006860Notes

Reaction equation

HRID 1006860 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][C:12]([N:14]3[CH2:18][C@H:17]([SH:19])[CH2:16][C@H:15]3[CH2:20][O:21][CH2:22][C:23]3[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=3[F:31])=[O:13])[C:5]=2[O:4][CH2:3][CH2:2]1.[C:32](Cl)(=[O:34])[CH3:33]>N1C=CC=CC=1>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][C:12]([N:14]3[CH2:18][C@H:17]([S:19][C:32](=[O:34])[CH3:33])[CH2:16][C@H:15]3[CH2:20][O:21][CH2:22][C:23]3[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=3[F:31])=[O:13])[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 10139099HCID 10139099, compound

Product 1

HCID 10141595HCID 10141595, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 10 g (21.96 mmol) (2S,4R)-4-Mercapto-2-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-1-carboxylic acid 2,3-dihydro-benzo [1,4]dioxin-5-yl ester in 130 ml pyridine were treated at 0° C. with 3.12 ml (43.92 mmol) acetyl chloride and stirred for 6 h at RT. The reaction was poured on ice water and extracted wit Et2O (3×). The organic phases were washed with aqueous 1 N HCl and 10% NaCl, dried (Na2SO4) and evaporated. Flash chromatography on silica gel (CH2Cl2/Et2O 99.5:0.5 to 98:2) gave 9.94 g (91%) (2S,4R)-4-Acetylsulfanyl-2-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidin-1-carboxylic acid 2,3-dihydro-benzo[1,4]dioxin-5-yl ester, MS: 498 (MH+).

Workup

  1. additionThe reaction was poured on ice water
  2. extractionextracted wit Et2O (3×)
  3. washThe organic phases were washed with aqueous 1 N HCl and 10% NaCl
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-94efef480af849d9a84a56567fed61e1
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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