Trifluoroacetic acid → Acetyl-{(R)-3-[3-fluoro-4-(2-methyl-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazol-5-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamic acid 1-phosphonooxy-ethyl ester

HRID 502534Notes

Reaction equation

HRID 502534 reaction equation
C([O:5][P:6]([O:41]C(C)(C)C)([O:8][CH:9]([O:11][C:12](=[O:40])[N:13]([C:37](=[O:39])[CH3:38])[CH2:14][C@@H:15]1[O:19][C:18](=[O:20])[N:17]([C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:34][C:33]4[C:29](=[N:30][N:31]([CH3:35])[CH:32]=4)[CH2:28]3)=[C:23]([F:36])[CH:22]=2)[CH2:16]1)[CH3:10])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[P:6]([O:8][CH:9]([O:11][C:12](=[O:40])[N:13]([C:37](=[O:39])[CH3:38])[CH2:14][C@@H:15]1[O:19][C:18](=[O:20])[N:17]([C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:34][C:33]4[C:29](=[N:30][N:31]([CH3:35])[CH:32]=4)[CH2:28]3)=[C:23]([F:36])[CH:22]=2)[CH2:16]1)[CH3:10])([OH:7])([OH:41])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68464915Acetyl-{(R)-3-[3-fluoro-4-(2-methyl-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazol-5-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamic acid 1-(di-tert-butoxy-phosphoryloxy)-ethyl ester

Product 1

HCID 24768948Acetyl-{(R)-3-[3-fluoro-4-(2-methyl-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazol-5-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamic acid 1-phosphonooxy-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 17b (1 equiv) in dichloromethane is added TFA (3 equiv) and the reaction mixture is stirred at rt for 3 h. The reaction mixture is concentrated in vacuo, and purified directly by HPLC (C-18 column, 10-100% gradient elution, MeCN:H2O) to give the title compound. Theoretical MS 542 (M+1)+

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. custompurified directly by HPLC (C-18 column, 10-100% gradient elution, MeCN:H2O)

Sources & evidence

ORD record
ord-acbf5d09b96d48c09bc61f34d8060d01
Source dataset
uspto-grants-2010_08
Patent number
US07776855B2

Reaction notes

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