Trifluoroacetic acid → [3-(4'-{(5S)-5-[(Acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-1,1'-biphenyl-4-yl)-4,5-dihydroisoxazol-5-yl]methyl dihydrogen phosphate

HRID 747244Notes

Reaction equation

HRID 747244 reaction equation
[P:1]([O:38]C(C)(C)C)([O:33]C(C)(C)C)([O:3][CH2:4][CH:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:26][C@H:25]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:24][C:23]4=[O:32])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:6]1)=[O:2].FC(F)(F)C(O)=O>ClCCl>[P:1]([OH:33])([OH:38])([O:3][CH2:4][CH:5]1[O:9][N:8]=[C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH2:26][C@H:25]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:24][C:23]4=[O:32])=[CH:20][CH:21]=3)=[CH:14][CH:15]=2)[CH2:6]1)=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69693473[3-(4'-{(5S)-5-[(Acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-1,1'-biphenyl-4-yl)-4,5-dihydroisoxazol-5-yl]methyl di-tert-butyl phosphate

Product 1

HCID 59749438[3-(4'-{(5S)-5-[(Acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-1,1'-biphenyl-4-yl)-4,5-dihydroisoxazol-5-yl]methyl dihydrogen phosphate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[3-(4′-{(5S)-5-[(Acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-1,1′-biphenyl-4-yl)-4,5-dihydroisoxazol-5-yl]methyl di-tert-butyl phosphate (95 mg, 0.16 mmol) was dissolved in dichloromethane (1 ml) and trifluoroacetic acid (0.1 ml) was added. The solution was stirred for 1 h at ambient temperature, then concentrated in vacuo. Dichloromethane was added and the volatiles were removed in vacuo. This was repeated twice with dichloromethane and five times with diethyl ether. A pale yellow solid was obtained (78 mg) corresponding to the desired product.

Workup

  1. concentrationconcentrated in vacuo
  2. additionDichloromethane was added
  3. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-708b8f1eb0aa40eda0bde534a7c1e55f
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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