Water → (S)-N-[[3-[3-Fluro-4-[1-(carbobenzyloxy)-3-azetidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1276461Notes

Reaction equation

HRID 1276461 reaction equation
[C:1]([N:11]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@@H:24]([CH2:26][N:27]=[N+]=[N-])[O:23][C:22]3=[O:30])=[CH:17][C:16]=2[F:31])[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1(P([C:45]2[CH:50]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH2:51]>C1COCC1>[F:31][C:16]1[CH:17]=[C:18]([N:21]2[CH2:25][C@H:24]([CH2:26][NH:27][C:50](=[O:51])[CH3:45])[O:23][C:22]2=[O:30])[CH:19]=[CH:20][C:15]=1[CH:13]1[CH2:14][N:11]([C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])[CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 18684851(S)-(-)-N-Carbobenzyloxy-3-[2-fluoro-4-[5-azidomethyl-2-oxo-3-oxazolidinyl]phenyl]azetidine

Product 1

HCID 18393166(S)-N-[[3-[3-Fluro-4-[1-(carbobenzyloxy)-3-azetidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-(-)-N-carbobenzyloxy-3-[2-fluoro-4-[5-azidomethyl-2oxo-3-oxazolidinyl]phenyl]azetidine (Example 81, Step 7, 1.63 g, 3.84 mmol) in dry THF (20 mL) was added triphenylphosphine (1.11 g, 4.23 mmol). After 3 hr, water (0.69 mL, 38.4 mmol) was added and the reaction stirred for 2 days at which time the solvents were evaporated. The residue was chromatographed over silica gel (150 g, 40-60 μm) eluting with 5-10% methanol-chloroform. The title compound was isolated as a viscous colorless oil. FAB-HRMS: theory 400.1672 (M+1); meas. 400.1676.

Workup

  1. customwere evaporated
  2. customThe residue was chromatographed over silica gel (150 g, 40-60 μm)
  3. washeluting with 5-10% methanol-chloroform

Sources & evidence

ORD record
ord-859a565425c04d3f9a92f85e30a3b25f
Source dataset
uspto-grants-2000_12
Patent number
US06166056

Reaction notes

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