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

HRID 1600382Notes

Reaction equation

HRID 1600382 reaction equation
C([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@H:10]([OH:13])[CH2:11][OH:12])=O)(C)(C)C.C(OC(N[C@@H](CC1C=CC=CC=1)[C@H](O)CO)=O)C1C=CC=CC=1>>[OH:12][CH2:11][C@H:10]1[O:13][C:6](=[O:5])[NH:8][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 9796935(2S,3S)-3-(benzyloxycarbonylamino)-4-phenylbutane-1,2-diolHCID 10967943(2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol

Product 1

HCID 9859125(4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinoneYield 70%

Procedure

The reaction procedure of Example 9 was repeated except that 434 mg (1.27 mmols) of (2S,3S)-3-(t-butoxycarbonylamino) -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 (4S,5S)-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-dd93a2ca822e422fa5b71b1acfb2d49f
Source dataset
uspto-grants-1998_04
Patent number
US05744630

Reaction notes

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