Water → HCID 67274354, compound

HRID 2193541Notes

Reaction equation

HRID 2193541 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:33][C@H:32]([CH2:34][N:35]=[N+]=[N-])[O:31][C:30]4=[O:38])=[CH:25][C:24]=3[F:39])[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P([C:53]2[CH:58]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH2:59]>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:33][C@H:32]([CH2:34][NH:35][C:58](=[O:59])[CH3:53])[O:31][C:30]4=[O:38])=[CH:25][C:24]=3[F:39])[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86597765HCID 86597765, compound

Product 1

HCID 67274354HCID 67274354, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.65 g of 4-{4-[4-{(5R)-5-azidomethyl-2-oxo-oxazolidin-3-yl}-2-fluoro-phenyl]-piperazin-1-yl}-piperidin-1-carboxylic acid benzyl ester (4.93 mmol), 1.55 g triphenylphosphine (5.91 mmol) and 0.88 g water (49.3 mmol) in 40 ml THF was stirred at reflux for 22 hrs. The reaction was controlled by TLC. The THF was evaporated and the residue dissolved in 10 ml acetic acid and 2 ml of acetic anhydride. the reaction was monitored by TLC. The solvents were evaporated and the residue crystallized from ethyl acetate.

Workup

  1. temperatureat reflux for 22 hrs
  2. customThe THF was evaporated
  3. dissolutionthe residue dissolved in 10 ml acetic acid
  4. customThe solvents were evaporated
  5. customthe residue crystallized from ethyl acetate

Sources & evidence

ORD record
ord-9903f6496ff24d7fb69f6863c744a092
Source dataset
uspto-grants-2012_12
Patent number
US08329908B2

Reaction notes

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