Sodium Hydroxide → (2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane

HRID 1858409Notes

Reaction equation

HRID 1858409 reaction equation
[CH2:1]([C@H:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C@H:9]([OH:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CC(C)=O>[CH2:1]([C@H:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C@@H:9]1[O:12][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71466451,1-Dimethylethyl N-((1S,2S)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl)carbamate2×

Product 1

HCID 9903372(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 0.976-g portion of the product obtained in Example 1, namely t-butyl [1(S)-benzyl-2(S)-hydroxy-3-chloropropyl]carbamate, was suspended in 8 ml of acetone, then 2 ml of 10% sodium hydroxide was added, and the mixture was stirred at room temperature for 1 hour. The aqueous layer was separated and the organic layer was concentrated to dryness to give t-butyl [1(S)-benzyl-2(S),3-epoxypropyl]carbamate. After purification by preparative TLC, the optical purity (99.8% ee) was confirmed using a chiral column.

Workup

  1. customThe aqueous layer was separated
  2. concentrationthe organic layer was concentrated to dryness

Sources & evidence

ORD record
ord-ab9d97d589c0446994d26c281868df03
Source dataset
uspto-grants-2000_11
Patent number
US06150567

Reaction notes

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