Sodium Hydroxide → HCID 178512167, compound

HRID 1414683Notes

Reaction equation

HRID 1414683 reaction equation
[NH:1]([C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[CH2:2][CH2:3][C:4]([NH:6][C@H:7]([C:18]([N:20]1[CH2:28][CH2:27][CH2:26][C@H:21]1[C:22]([O:24]C)=[O:23])=[O:19])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:17])[NH:13][N+:14]([O-:16])=[O:15])=[O:5].[OH-].[Na+]>CC(C)=O>[NH:1]([C:29]([O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:30])[CH2:2][CH2:3][C:4]([NH:6][C@H:7]([C:18]([N:20]1[CH2:28][CH2:27][CH2:26][C@H:21]1[C:22]([OH:24])=[O:23])=[O:19])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:17])[NH:13][N+:14]([O-:16])=[O:15])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501300HCID 178501300, compound

Product 1

HCID 178512167HCID 178512167, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 30 ml. of acetone was dissolved 2.82 g. of Z-β-Ala-Arg(NO2)-Pro-OMe and, under cooling with ice, 10.7 ml. of 1N aqueous sodium hydroxide was added. The mixture was stirred at room temperature for 2 hours. After the mixture was neutralized with 11 ml. of 1N hydrochloric acid, the acetone was distilled off under reduced pressure. To the oily residue was added 30 ml. of cold water and the water was removed by decantation. The residue was washed once with cold water and dried. It was then chromatographed on a column of silica gel (90 g.) with a developer solvent, ethyl acetate-pyridine-acetic acid-water(60:20:6:11). The fractions rich in the contemplated compound were pooled and concentrated to dryness under reduced pressure. The residue was washed with ether and collected by filtration. Yield 2.62 g., melting point: 65°-67° C; [α]D22 -27.5° (c=1.07 %, DMF).

Workup

  1. distillationof 1N hydrochloric acid, the acetone was distilled off under reduced pressure
  2. additionTo the oily residue was added 30 ml
  3. customof cold water and the water was removed by decantation
  4. washThe residue was washed once with cold water
  5. customdried
  6. customIt was then chromatographed on a column of silica gel (90 g.) with a developer solvent, ethyl acetate-pyridine-acetic acid-water(60:20:6:11)
  7. concentrationconcentrated to dryness under reduced pressure
  8. washThe residue was washed with ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e4af8315a3e444909eb54205b0b632f6
Source dataset
uspto-grants-1977_01
Patent number
US04001199

Reaction notes

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