Water → HCID 69980407, compound

HRID 1167474Notes

Reaction equation

HRID 1167474 reaction equation
[Si]([O:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][O:26][C:27]4[CH:31]=[CH:30][O:29][N:28]=4)[O:22][C:21]3=[O:32])=[CH:16][C:15]=2[F:33])[CH2:10]1)(C(C)(C)C)(C)C.O>C(O)(=O)C>[OH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][O:26][C:27]4[CH:31]=[CH:30][O:29][N:28]=4)[O:22][C:21]3=[O:32])=[CH:16][C:15]=2[F:33])[CH2:10]1

Participants

4

Reactant 2

HCID 962WaterHCID 57151580HCID 57151580, compound

Product 1

HCID 69980407HCID 69980407, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-(4-((3R)-3-t-Butyldimethylsilyloxy-1-pyrrolidinyl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one (1.8 g, 3.77 mmol) was stirred in a mixture of acetic acid, water, and tetrahydroftiran (3:1:1, 40 ml) at 90° for four hours. Solvent was evaporated, and the residue purified by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 10% MeOH in dichloromethane. Relevant fractions were combined and evaporated to givc the desired product (420 mg) as a foam. MS (ESP): 364 (MH+) for C17H18FN3O5.

Workup

  1. customSolvent was evaporated
  2. customthe residue purified by chromatography on a 10 g silica Mega Bond Elut® column
  3. washeluting with
  4. temperaturea gradient increasing in polarity from 0 to 10% MeOH in dichloromethane
  5. customevaporated

Sources & evidence

ORD record
ord-a77919f9ccbb4e31a9e24606b9ea300d
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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