HCID 12851922, compound → HCID 20280794, compound

HRID 1248064Notes

Reaction equation

HRID 1248064 reaction equation
C([S:4][CH2:5][CH:6]([CH3:27])[C:7]([N:9]([CH:14]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=2)[CH2:16][CH2:15]1)[CH2:10][C:11]([OH:13])=[O:12])=[O:8])(=O)C>N>[SH:4][CH2:5][CH:6]([CH3:27])[C:7]([N:9]([CH:14]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=2)[CH2:16][CH2:15]1)[CH2:10][C:11]([OH:13])=[O:12])=[O:8]

Participants

3

Reactant 1

HCID 12851922HCID 12851922, compound

Product 1

HCID 20280794HCID 20280794, compoundYield 738.5%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

N-(3-Acetylthio-2-methylpropionyl)-N-(5,6-dimethoxy-1-indanyl)glycine (1.0 g) is dissolved in 50 ml of 5.5N methanolic ammonia, and the mixture is stirred at room temperature for 2 hours. The reaction mixture is concentrated at 40° C. under reduced pressure, and the residue is dissolved in 10 ml of water, made acidic with 10% hydrochloric acid, and extracted with 200 ml of ethyl acetate. The extract is washed with water, dried, and then treated with activated carbon. After ethyl acetate is distilled off under reduced pressure, a mixture of ethyl ether and petroleum ether is added to the residue to give 6.6 g of N-(3-mercapto-2-methylpropionyl)-N-(5,6-dimethoxy-1-indanyl)glycine as colorless powder.

Workup

  1. concentrationThe reaction mixture is concentrated at 40° C. under reduced pressure
  2. dissolutionthe residue is dissolved in 10 ml of water
  3. extractionextracted with 200 ml of ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. additiontreated with activated carbon
  7. distillationAfter ethyl acetate is distilled off under reduced pressure
  8. additiona mixture of ethyl ether and petroleum ether
  9. additionis added to the residue

Sources & evidence

ORD record
ord-a32dac9177b64ebda1baf9c293ca9453
Source dataset
uspto-grants-1985_06
Patent number
US04521607

Reaction notes

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