Water → HCID 67274191, compound

HRID 1163347Notes

Reaction equation

HRID 1163347 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([N:15]([C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:36][C@H:35]([CH2:37][N:38]=[N+]=[N-])[O:34][C:33]3=[O:41])=[CH:28][C:27]=2[F:42])[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:43].C1(P([C:57]2[CH:62]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([N:15]([C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:36][C@H:35]([CH2:37][NH:38][C:62](=[O:43])[CH3:57])[O:34][C:33]3=[O:41])=[CH:28][C:27]=2[F:42])[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86597766HCID 86597766, compound

Product 1

HCID 67274191HCID 67274191, compound

Procedure

A solution of 1.15 g 3-{[4-{(5R)-5-azidomethyl-2-oxo-oxazolidin-3-yl}-2-fluoro-phenyl]-benzyloxycarbonyl-amino)-azetidine-1-carboxylic acid benzyl ester (2 mmol), 0.36 ml water (20 mmol) and 0.277 g triphenylphosphine (2.2 mmol) was stirred for 16 h at 50° C. The solvent was evaporated. The residue was dissolved in 5 ml acetic acid and 2 ml acetic anhydride. The solution was stirred for 30 min and evaporated. The residue was purified by chromatography using a 9/1 ethyl acetate/methanol mixture as eluent.

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in 5 ml acetic acid
  3. customevaporated
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-977805d2166f4cd896d5a999a2260957
Source dataset
uspto-grants-2010_10
Patent number
US07820823B2

Reaction notes

Loading…