Hydrochloric Acid → HCID 14862511, compound

HRID 1870262Notes

Reaction equation

HRID 1870262 reaction equation
C[O:2][C:3]([CH2:5][C@H:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:9][CH2:8][CH2:7]1)=[O:4].[OH-].[Na+].Cl>CO>[C:3]([CH2:5][C@H:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)(=[O:18])=[O:19])[CH2:9][CH2:8][CH2:7]1)([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57040607HCID 57040607, compound

Product 1

HCID 14862511HCID 14862511, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (5S)-5-methoxycarbonylmethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.20 g), a 5% aqueous sodium hydroxide solution (10 ml) and methanol (10 ml) is heated with stirring at 80° C. for three hours. To the reaction solution is added ice, and the mixture is acidified with conc. hydrochloric acid, and extracted with dichloromethane. The extract is dried over sodium sulfate, and concentrated under reduced pressure to remove the solvent to give (5S)-5-carboxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.19 g).

Workup

  1. additionTo the reaction solution is added ice
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract is dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-54487cf5a4074ca59b728abb0ed78c78
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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