Anisole → 1-[(2R)-3-(Acetylthio)-2-methyl-1-oxopropyl]-D-proline

HRID 1871700Notes

Reaction equation

HRID 1871700 reaction equation
C([O:5][C:6]([CH:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:21])[CH:14]([CH3:20])[CH2:15][S:16][C:17](=[O:19])[CH3:18])=[O:7])(C)(C)C.C1(OC)C=CC=CC=1>>[C:17]([S:16][CH2:15][C@H:14]([CH3:20])[C:13]([N:9]1[CH2:10][CH2:11][CH2:12][C@@H:8]1[C:6]([OH:7])=[O:5])=[O:21])(=[O:19])[CH3:18]

Participants

3

Reactant 2

HCID 7519AnisoleHCID 14181515HCID 14181515, compound

Product 1

HCID 6890171-[(2R)-3-(Acetylthio)-2-methyl-1-oxopropyl]-D-proline

Procedure

18.9 g (60.0 mmol) 1-(3-acetylsulfanyl-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid tert-butyl ester were stirred with 120 ml trifluoric acid and 75 ml anisole under argon for three hours. The mixture was evaporated under vacuum. The residue was dissolved in icecold ethylacetate and washed with an icecold aqueous solution of sodiumbicarbonate. Concentrated hydrochloric acid was added unter icecooling until ph 2-3. The aqueous phase was extracted three times with icecold ethylacetate, dried with sodium sulfate and evaporated. The yield was 15.3 g (98%) 1-[(R)3-acetylsulfanyl-2-methyl-propionyl]-(R)-pyrrolidine-2-carboxylic acid that was used without further purification. [a]D =+127.8° (1% EtOH).

Workup

  1. customThe mixture was evaporated under vacuum
  2. dissolutionThe residue was dissolved in icecold ethylacetate
  3. washwashed with an icecold aqueous solution of sodiumbicarbonate
  4. additionConcentrated hydrochloric acid was added unter icecooling until ph 2-3
  5. extractionThe aqueous phase was extracted three times with icecold ethylacetate
  6. dry with materialdried with sodium sulfate
  7. customevaporated
  8. customThe yield was 15.3 g (98%) 1-[(R)3-acetylsulfanyl-2-methyl-propionyl]-(R)-pyrrolidine-2-carboxylic acid that was used without further purification
  9. custom[a]D =+127.8° (1% EtOH)

Sources & evidence

ORD record
ord-989b09199d154676b5ec7a19081c72f7
Source dataset
uspto-grants-2000_08
Patent number
US06103910

Reaction notes

Loading…