Sodium Hydroxide → HCID 10764619, compound

HRID 1378453Notes

Reaction equation

HRID 1378453 reaction equation
C([O:5][C:6](=[O:33])[C@H:7]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[NH:8][C:9]([C:11]1([NH:16][C:17]([C:19]2([SH:24])[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])CCC.[OH-].[Na+]>CO>[SH:24][C:19]1([C:17]([NH:16][C:11]2([C:9]([NH:8][C@H:7]([C:6]([OH:33])=[O:5])[CH2:25][C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)=[O:10])[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:18])[CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10552575HCID 10552575, compound

Product 1

HCID 10764619HCID 10764619, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-[[1-[[(1-mercapto-1-cyclopentyl)carbonyl]amino]-1-cyclopentyl]carbonyl]-L-tyrosine butyl ester (0.47 g, 0.99 mmol) in degassed methanol is added 1N sodium hydroxide (3.00 mL, 3.00 mmol). The mixture is stirred for 17 hours. The solvent is removed in vacuo and water (30 mL) is added to the residue. The aqueous phase is washed with ethyl acetate (10 mL) and then acidified to pH 1 with 1N hydrochloric acid. The aqueous phase is extracted with ethyl acetate (3×50 mL), washed with brine and dried over magnesium sulfate. The solvent is removed in vacuo to afford a foam which is crystallized from hexane/ethyl acetate to give N-[[1-[[(1-mercapto-1-cyclopentyl)carbonyl]amino]-1-cyclopentyl]carbonyl]-L-tyrosine, m.p. 90° C.

Workup

  1. customThe solvent is removed in vacuo and water (30 mL)
  2. additionis added to the residue
  3. washThe aqueous phase is washed with ethyl acetate (10 mL)
  4. extractionThe aqueous phase is extracted with ethyl acetate (3×50 mL)
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent is removed in vacuo
  8. customto afford a foam which
  9. customis crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-d37ae882e22b40f3aad8c246b44cbedb
Source dataset
uspto-grants-1997_09
Patent number
US05668158

Reaction notes

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