Sodium Hydroxide → HCID 22822721, compound

HRID 1758840Notes

Reaction equation

HRID 1758840 reaction equation
C[O:2][C:3]([C@@H:5]([NH:10][CH:11]([C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([OH:19])=[O:18])=[O:14])[CH3:12])[CH2:6][CH2:7][S:8][CH3:9])=[O:4].[OH-].[Na+]>O>[C:3]([C@@H:5]([NH:10][C@H:11]([C:13]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([OH:19])=[O:18])=[O:14])[CH3:12])[CH2:6][CH2:7][S:8][CH3:9])([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22822731HCID 22822731, compound

Product 1

HCID 22822721HCID 22822721, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-(1(S)-methoxycarbonyl-3-methylthiopropyl)-DL-alanyl-L-proline (127.5 mg; 0.384 mM) in 2 ml of water is treated under nitrogen with 7.82 ml 0.100 N sodium hydroxide (0.782 mM) and stirred for 21/2 hr. at room temperature. The product is absorbed from the reaction mixture onto 30 ml of Dowex 50 (H+) and eluted with 4% aqueous pyridine to yield 73.5 mg., which is further purified over a LH-B 20 column to yield 55.7 mg. of product. The nmr spectrum in D2O shows S-CH3 at 2.1; CH-CH3 at 1.5 and 1.6δ and no methyl ester. The mass spectrogram on silylated material shows the expected molecular ion at 462 m/e.

Workup

  1. customat room temperature
  2. customThe product is absorbed from the reaction mixture onto 30 ml of Dowex 50 (H+)
  3. washeluted with 4% aqueous pyridine
  4. customto yield 73.5 mg
  5. custom, which is further purified over a LH-B 20 column
  6. customto yield 55.7 mg

Sources & evidence

ORD record
ord-88163d1836864fabadaf8360bf8eeb1c
Source dataset
uspto-grants-1983_02
Patent number
US04374829

Reaction notes

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