Sodium Hydroxide → HCID 13477465, compound

HRID 3757Notes

Reaction equation

HRID 3757 reaction equation
[OH-].[Na+].C([S:6][CH2:7][CH:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=[O:17])=[O:10])(=O)C>CO.C(OCC)(=O)C>[SH:6][CH2:7][CH:8]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14155009HCID 14155009, compound

Product 1

HCID 13477465HCID 13477465, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1N Sodium hydroxide (12.9 ml., 3.8 equiv.) is added dropwise over 10 minutes to a chilled solution (ice bath) of the product from part (b) (1.20 g., 3.41 mmole) dissolved in methanol (13 ml.) under a nitrogen atmosphere. The mixture is stirred at 0° for 10 minutes and then allowed to warm to room temperature and stirred for 3 hours. The mixture is concentrated to half volume in vacuo. The residue is diluted with water (40 ml.) washed with chloroform (2×20 ml.), and acidified to a pH of about 1.5 with concentrated hydrochloric acid. The resulting white suspension is extracted with ethyl acetate (3×15 ml.). These organic extracts are combined, washed with water and brine (20 ml. each), dried (Na2SO4) and concentrated to yield a white waxy solid (0.82 g.). This solid is dissolved in ethyl acetate, filtered, concentrated and the residue triturated with ether to give (±)-5-[[2-(mercaptomethyl)-1-oxo-3-phenylpropyl]amino] pentanoic acid as white solids; m.p. 78°-79°. TLC (silica gel, 4:1 benzene/acetic acid) Rf =0.30 (slight tailing).

Workup

  1. stirringstirred for 3 hours
  2. concentrationThe mixture is concentrated to half volume in vacuo
  3. additionThe residue is diluted with water (40 ml.)
  4. washwashed with chloroform (2×20 ml.)
  5. extractionThe resulting white suspension is extracted with ethyl acetate (3×15 ml.)
  6. washwashed with water and brine (20 ml
  7. dry with materialeach), dried (Na2SO4)
  8. concentrationconcentrated
  9. customto yield a white waxy solid (0.82 g.)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customthe residue triturated with ether

Sources & evidence

ORD record
ord-769057d21a9f49c2a23e796d958b008c
Source dataset
uspto-grants-1988_02
Patent number
US04722810

Reaction notes

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