Sodium Hydroxide → HCID 13135339, compound

HRID 621184Notes

Reaction equation

HRID 621184 reaction equation
Cl.C([O:4][C:5]([CH:7]([NH:20][C@H:21]([C:23]([N:25]([CH:30]1[CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31]1)[CH2:26][C:27]([OH:29])=[O:28])=[O:24])[CH3:22])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)=[O:6])C.[OH-].[Na+]>CO>[C:5]([CH:7]([NH:20][C@H:21]([C:23]([N:25]([CH:30]1[CH2:31][C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:38]1)[CH2:26][C:27]([OH:29])=[O:28])=[O:24])[CH3:22])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)([OH:6])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13132319HCID 13132319, compound

Product 1

HCID 13135339HCID 13135339, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[1-Ethoxycarbonyl-3-(3,4-dimethoxyphenyl)propyl]-L-alanyl-N-(indan-2-yl)glycine hydrochloride (1.1 g) is dissolved in 30 ml of methanol. To the solution is added 5 ml of 2N aqueous sodium hydroxide. After stirring for 4 hours, the reaction mixture is concentrated, and 30 ml of water is added. On adjusting the pH to about 5 with diluted hydrochloric acid, an oily substance separates, which is extracted with ethyl acetate. The extract is washed with water, dried and concentrated. Methanol (4 ml) is added to the residue, and the mixture is allowed to stand. There is obtained 60 mg of N-[1-carboxy-3-(3,4-dimethoxyphenyl)propyl]-L-alanyl-N-(indan-2-yl)glycine as crystals melting at 160°-165° C. with decomposition.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. addition30 ml of water is added
  3. extractionan oily substance separates, which is extracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. concentrationconcentrated
  7. additionMethanol (4 ml) is added to the residue

Sources & evidence

ORD record
ord-65ed6df5eed94b0a8587d17fd7584f51
Source dataset
uspto-grants-1989_04
Patent number
US04822818

Reaction notes

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