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

HRID 1738731Notes

Reaction equation

HRID 1738731 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%). 1H NMR(500 MHz, CDCl3) δ ppm 7.29-7.06(m, 10H), 5.08(d, 1H, J=9.5 Hz), 3.77(d, 1H, J=10.1 Hz), 3.65(broad q, 1H), 3.01 (m, 1H), 2.86(d, 2H, J=8.0 Hz), 2.77(dd, 1 H, J=1 3.6, 4.6 Hz), 2.40(dd, 1H, J=13.6, 8.5 Hz), 1.55-1.39(m 2H), 1.42(s, 9H).

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-1262cfddaddb44f99b420371218a28d0
Source dataset
uspto-grants-1999_10
Patent number
US05962692

Reaction notes

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