Water → HCID 67274354, compound

HRID 1163339Notes

Reaction equation

HRID 1163339 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-6be535056419476a98079d54fc2e7ce9
Source dataset
uspto-grants-2010_10
Patent number
US07820823B2

Reaction notes

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