Water → HCID 54424107, compound

HRID 1004812Notes

Reaction equation

HRID 1004812 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][N:26]=[N+]=[N-])[O:22][C:21]3=[O:29])=[CH:16][C:15]=2[F:30])[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[CH3:4][C:2]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH2:26])[O:22][C:21]3=[O:29])=[CH:16][C:15]=2[F:30])[CH2:12][CH2:13]1)=[O:7])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 54198623HCID 54198623, compound

Product 1

HCID 54424107HCID 54424107, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-(-)-4-[4-[5-(azidomethyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (EXAMPLE 20, Step 7, 12.05 g) in dry tetrahydrofuran (96 mL) under N2 is treated with triphenylphosphine (8.29 g) over five minutes, and the resulting mixture is stirred at ambient temperature for two hours. The mixture is then treated with water (3.1 mL), heated up to 40° C., stirred at 40° C. for five hours and at ambient temperature for 12 hours, and then concentrated under reduced pressure to give a viscous oil which is chromatographed on silica gel (70-230 mesh, 500 g), eluting with a gradient of methanol/methylene chloride (2.5/97.5-15/85). Pooling and concentration of those fractions with an Rf =0.26 by TLC (methanol/chloroform, 10/90) gives the title compound, mp 136-137° C.

Workup

  1. temperatureheated up to 40° C.
  2. stirringstirred at 40° C. for five hours and at ambient temperature for 12 hours
  3. concentrationconcentrated under reduced pressure
  4. customto give a viscous oil which
  5. customis chromatographed on silica gel (70-230 mesh, 500 g)
  6. washeluting with a gradient of methanol/methylene chloride (2.5/97.5-15/85)

Sources & evidence

ORD record
ord-97d361f49de44465aace7848818c43eb
Source dataset
uspto-grants-2000_04
Patent number
US06051716

Reaction notes

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