(2S,3S)-3-(benzyloxycarbonylamino)-4-phenylbutane-1,2-diol → (4R,5R)-5-hydroxymethyl-4-phenylmethyloxazolidinone

HRID 1600383Notes

Reaction equation

HRID 1600383 reaction equation
C([O:8][C:9]([NH:11][C@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:13]([OH:16])[CH2:14][OH:15])=O)C1C=CC=CC=1.C(OC(N[C@@H](CC1C=CC=CC=1)[C@H](O)CO)=O)C1C=CC=CC=1>>[OH:15][CH2:14][C@@H:13]1[O:16][C:9](=[O:8])[NH:11][C@@H:12]1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 9796935(2S,3S)-3-(benzyloxycarbonylamino)-4-phenylbutane-1,2-diolHCID 54284814(2R,3R)-3-(benzyloxycarbonylamino)-4-phenylbutane-1,2-diol

Product 1

HCID 53823725(4R,5R)-5-hydroxymethyl-4-phenylmethyloxazolidinoneYield 70%

Procedure

The reaction procedure of Example 9 was repeated except that 400 mg (1.27 mmols) of (2R,3R)-3-(benzyloxycarbonylamino)-4-phenylbutane-1,2-diol was used in lieu of 400 mg (1.27 mmols) of (2S,3S)-3-(benzyloxycarbonylamino)-4-phenylbutane-1,2-diol and the reaction product was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to provide (183 mg (0.887 mmol, yield 70%) of (4R,5R)-5-hydroxymethyl-4-phenylmethyloxazolidinone as crystals.

Workup

  1. customThe reaction procedure of Example 9
  2. customthe reaction product was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-c00e71d198e746f3b6cb68bfee57b1f9
Source dataset
uspto-grants-1998_04
Patent number
US05744630

Reaction notes

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