Sodium Hydroxide → 1,1-Dimethylethyl N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]carbamate

HRID 850857Notes

Reaction equation

HRID 850857 reaction equation
C(O)(=O)C(O)=O.[C:7]([O:11][C:12]([NH:14][C@H:15]([C@@H:23]([OH:34])[CH2:24][C@@H:25]([NH2:33])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:7]([O:11][C:12]([NH:14][C@H:15]([C@@H:23]([OH:34])[CH2:24][C@@H:25]([NH2:33])[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70191891HCID 70191891, compound

Product 1

HCID 103178781,1-Dimethylethyl N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(2S,3S,5S)-2-tert-Butoxycarbonylamino-3-hydroxy-5-amino-1,6-diphenylhexane oxalate (500 mg, 1.05 mmol) obtained in Example 43 (A) was suspended in toluene (5 ml). An aqueous solution (5 ml) of NaOH (200 mg) was added thereto and the mixture was vigorously stirred, then separated. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the filtrate was concentrated to give the desired compound as colorless crystals. Yield: 340 mg (84%).

Workup

  1. customseparated
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-46a79619164e4a008046c648909a75d9
Source dataset
uspto-grants-2000_01
Patent number
US06018069

Reaction notes

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