Dichloromethane methanol → HCID 86754374, compound

HRID 1584412Notes

Reaction equation

HRID 1584412 reaction equation
C([O:5][NH:6][C:7](=[O:34])[C@@H:8]([NH:26][C:27](=[O:33])[C@H:28]([CH:30]([CH3:32])[CH3:31])[NH2:29])[CH2:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11])(C)(C)C.CO.C(Cl)[Cl:38]>ClCCCl>[ClH:38].[OH:5][NH:6][C:7](=[O:34])[C@@H:8]([NH:26][C:27](=[O:33])[C@H:28]([CH:30]([CH3:32])[CH3:31])[NH2:29])[CH2:9][S:10]([C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:18]=1)(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 21226129Dichloromethane methanolHCID 86754373HCID 86754373, compound

Product 1

HCID 86754374HCID 86754374, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of (R)-N-tert-butoxy-2-valinamido-3-(4-phenoxyphenylsulfonyl)-propionamide (1.6 g) in 1,2-dichloroethane (50 ml) was cooled to -20° C. and bubbled for 15-20 minutes with hydrochloric acid gas in a pressure tube. The flask was then sealed and the mixture stirred for 24 hours. After cooling the tube was cautiously vented and its contents evaporated to yield a gum, which upon trituration with ethyl acetate gave a crude product as a white powder. This product was stirred overnight with 10% methanol/methylene chloride (20 ml) and filtered to remove impurities. This was repeated three times to give (R)-N-hydroxy-2-valinamido-3-(4-phenoxyphenylsulfonyl)-propionamide hydrochloride (760 mg), m.p. 214-217° C.

Workup

  1. custombubbled for 15-20 minutes with hydrochloric acid gas in a pressure tube
  2. customThe flask was then sealed
  3. temperatureAfter cooling the tube
  4. customits contents evaporated
  5. customto yield a gum, which upon trituration with ethyl acetate
  6. customgave a crude product as a white powder
  7. filtrationfiltered
  8. customto remove impurities

Sources & evidence

ORD record
ord-38c2aec08fe54dffb75160d984e2ad4a
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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