Water → D-2-Amino-5-phenyl-pentanoic acid

HRID 1068835Notes

Reaction equation

HRID 1068835 reaction equation
O[C@@H](C1C=CC=CC=1)[C@@H](N(C)[C:6](=[O:18])[C@H:7]([NH2:17])[CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C.[OH2:26]>>[NH2:17][C@H:7]([CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:6]([OH:18])=[O:26]

Participants

3

Reactant 2

HCID 962Water2×HCID 536999852(R)-Amino-5-phenyl-pentanoic acid (2(S)-hydroxy-1(S)-methyl-2-phenyl-ethyl)-methyl-amide

Product 1

HCID 6993756D-2-Amino-5-phenyl-pentanoic acid

Procedure

A solution of the compound of Example 199, Step A (400 mg, 1.18 mmol) in water (10 mL) was heated to reflux for 20 h. The reaction was diluted with water (20 mL) and extracted with CH2Cl2 (2×20 mL). The combined organic extracts were back extracted with water (2×20 mL) and the combined aqueous extracts were concentrated down to a white solid. The solid was triturated with EtOH to remove residual pseudoephedrine and deliver Example 199, Step B (135 mg, 60%): +APcl MS (M+1)+ 194.

Workup

  1. temperatureto reflux for 20 h
  2. extractionextracted with CH2Cl2 (2×20 mL)
  3. extractionThe combined organic extracts were back extracted with water (2×20 mL)
  4. concentrationthe combined aqueous extracts were concentrated down to a white solid
  5. customThe solid was triturated with EtOH
  6. customto remove residual pseudoephedrine

Sources & evidence

ORD record
ord-e08730572def4794941bc89727c6b2d2
Source dataset
uspto-grants-2001_06
Patent number
US06251902B1

Reaction notes

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