1,2-Dichloroethane → HCID 86754376, compound

HRID 1584415Notes

Reaction equation

HRID 1584415 reaction equation
C([O:5][NH:6][C:7](=[O:29])[C@@H:8]([N:26]([CH3:28])[CH3:27])[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.[Cl:30]CCCl>>[ClH:30].[CH3:27][N:26]([CH3:28])[C@@H:8]([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:11])=[O:12])[C:7]([NH:6][OH:5])=[O:29]

Participants

3

Reactant 2

HCID 111,2-DichloroethaneHCID 54553860HCID 54553860, compound

Product 1

HCID 86754376HCID 86754376, compound

Conditions

Temperature
-30 °C

Procedure

This compound, (R)-N-tert-butoxy-2-dimethylamino-3-(4-phenoxyphenylsulfonyl)-propionamide, was dissolved in 1,2-dichloroethane (50 ml), cooled to -30° C. and bubbled for 15-20 minutes with hydrochloric acid gas in a pressure tube. The flask was then sealed and the mixture stirred overnight. After cooling the tube was cautiously vented and its contents evaporated, to yield a gum, which upon trituration with 2:1 hexane/ethyl acetate gave a white powder, (R)-2-dimethylamino-N-hydroxy-3-(4-phenoxyphenylsulfonyl)-propionamide hydrochloride (0.43 g), m.p. 65-70° 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 2:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-9b0455c51df84156ba56c603664837e0
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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