Potassium Hydroxide → N-[3-carboxy-2-(2-methylpropyl)propanoyl]-O-methyl-L-tyrosine N-methylamide

HRID 745619Notes

Reaction equation

HRID 745619 reaction equation
[CH3:1][NH:2][C:3](=[O:28])[C@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[NH:5][C:6](=[O:18])[CH:7]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:8][C:9]([O:11]CC)=[O:10].[OH-].[K+]>CO>[CH3:1][NH:2][C:3](=[O:28])[C@H:4]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[NH:5][C:6](=[O:18])[CH:7]([CH2:14][CH:15]([CH3:16])[CH3:17])[CH2:8][C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14303040N-[3-(ethoxycarbonyl)-2-(2-methylpropyl)propanoyl]-O-methyl-L-tyrosine N-methylamide

Product 1

HCID 14303042N-[3-carboxy-2-(2-methylpropyl)propanoyl]-O-methyl-L-tyrosine N-methylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[3-(Ethoxycarbonyl)-2-(2-methylpropyl)propanoyl]-O-methyl-L-tyrosine N-Methylamide (4.7 g., 0.012 mol.) was suspended in methanol (25 mls.) containing potassium hydroxide solution (12 mls. of 1M). The mixture was stirred overnight and the solvent was removed by evaporation in vacuo to yield a gum. The gum was partitioned between diethyl ether (50 mls.) and sodium bicarbonate solution (50 mls.). The aqueous phase was separated, washed with ethyl ether (50 mls.) and adjusted to pH 2 by the addition of dilute hydrochloric acid. The aqueous mixture was extracted with dichloromethane (3×100 mls.) and the extracts combined and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation in vacuo to yield a gum (3.3 g.). The gum was recrystallized from a mixture of dichloromethane and hexane to yield N-[3-carboxy-2-(2-methylpropyl)propanoyl]-O-methyl-L-tyrosine N-methylamide as a white solid which was a mixture of two diastereomers. (m.p. 92°-96° C. Found: C, 61.7; H, 7.6; N, 7.5%. C19H28N2O5 0.3H2O requires C, 61.7; H, 7.8; N, 7.6%).

Workup

  1. customthe solvent was removed by evaporation in vacuo
  2. customto yield a gum
  3. customThe gum was partitioned between diethyl ether (50 mls.) and sodium bicarbonate solution (50 mls.)
  4. customThe aqueous phase was separated
  5. washwashed with ethyl ether (50 mls.)
  6. additionadjusted to pH 2 by the addition of dilute hydrochloric acid
  7. extractionThe aqueous mixture was extracted with dichloromethane (3×100 mls.)
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed by evaporation in vacuo
  10. customto yield a gum (3.3 g.)
  11. customThe gum was recrystallized from a mixture of dichloromethane and hexane

Sources & evidence

ORD record
ord-0ba7fa4fb41743ff9e5c321c1d0d2fd4
Source dataset
uspto-grants-1986_07
Patent number
US04599361

Reaction notes

Loading…