Sodium Hydroxide → SQ 28603

HRID 3755Notes

Reaction equation

HRID 3755 reaction equation
C([S:4][CH2:5][CH:6]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]([O:14]CC)=[O:13])=[O:8])(=O)C.[OH-].[Na+].C1(C)C=CC=CC=1.C(O)(=O)C>CO>[SH:4][CH2:5][CH:6]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:8]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 13477460(+/-)-3-[[2-[(Acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]propanoic acid, ethyl esterHCID 18331056Acetic acid toluene

Product 1

HCID 123742SQ 28603

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product from part (a) (1.02 g., 3.02 mmole) in methanol (6 ml.) is chilled (ice/methanol) and to it, under nitrogen, is added 1N sodium hydroxide (6.35 ml.) over 15 minutes. The mixture is stirred for 3 hours while warming to room temperature (TLC indicates incomplete reaction), and additional 1N sodium hydroxide (3.0 ml.) is added in one portion. After stirring for an additional 3 hours at room temperature, the mixture is concentrated to approximately 1/2 volume in vacuo, and the residue is partitioned between water (50 ml.) and ethyl acetate (30 ml.). The aqueous layer is washed with ethyl acetate (30 ml.), adjusted to a pH of about 2 with concentrated hydrochloric acid, and extracted again with ethyl acetate (3×20 ml.). These organic layers are pooled, washed with water and brine (30 ml. each), dried (Na2SO4), and concentrated in vacuo to yield 0.71 g. of (±)-3-[[2-(mercaptomethyl)-1-oxo- -phenylpropyl]amino]propanoic acid as a white solid; m.p. 76°-82°. TLC (silica gel, toluene/acetic acid; (4:1) Rf =0.37, minor spot at 0.07.

Workup

  1. additionis added in one portion
  2. stirringAfter stirring for an additional 3 hours at room temperature
  3. concentrationthe mixture is concentrated to approximately 1/2 volume in vacuo
  4. customthe residue is partitioned between water (50 ml.) and ethyl acetate (30 ml.)
  5. washThe aqueous layer is washed with ethyl acetate (30 ml.)
  6. extractionextracted again with ethyl acetate (3×20 ml.)
  7. washwashed with water and brine (30 ml
  8. dry with materialeach), dried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customto yield 0.71 g

Sources & evidence

ORD record
ord-8fea9f03fff34b1c8f6436c578cdb536
Source dataset
uspto-grants-1988_02
Patent number
US04722810

Reaction notes

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