Acetic Acid → HCID 10195267, compound

HRID 2306616Notes

Reaction equation

HRID 2306616 reaction equation
C[O-].[Na+].[C:4]([NH:7][CH2:8][CH:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[S:22][CH:23]([C:28]4[CH:33]=[CH:32][C:31]([O:34]S(C)(=O)=O)=[CH:30][CH:29]=4)[C:24](=[O:27])[NH:25][N:26]=3)=[C:17]([F:39])[CH:16]=2)[CH2:10]1)(=[O:6])[CH3:5].C(O)(=O)C>CO>[F:39][C:17]1[CH:16]=[C:15]([N:11]2[CH2:10][C@H:9]([CH2:8][NH:7][C:4](=[O:6])[CH3:5])[O:13][C:12]2=[O:14])[CH:20]=[CH:19][C:18]=1[C:21]1[S:22][CH:23]([C:28]2[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=2)[C:24](=[O:27])[NH:25][N:26]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 23529054HCID 23529054, compound

Product 1

HCID 10195267HCID 10195267, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

25% Sodium methoxide solution in methanol (0.027 ml, 0.117 mmol) is added to methanesulfonic acid 4-(2-{4-[5-(acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2-fluorophenyl}-5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-6-yl)-phenyl ester (0.050 g, 0.0932 mmol) in methanol (2 ml) and the mixture is stirred at room temperature overnight. The reaction mixture is neutralized with acetic acid (0.020 ml), evaporated to dryness and the residue is purified by PTLC (10% MeOH/DCM) to give product as a white solid (0.039 g, 92%); 1H NMR (300 MHz, DMSO-d6) δ 1.80 (s, 3H), 3.40-3.45 (bs, 2H), 3.74 (dd, J=6.9, 10.5 Hz, 1H), 4.12 (t, J=9.3 Hz, 1H), 4.70-4.79 (m, 1H), 4.98 (s, 3H), 6.73 (d, J=8.4 Hz, 2H), 7.08 (d, J=8.7 Hz, 1H), 7.37 (dd, J=1.8, 8.7 Hz, 1H), 7.55-7.60 (m, 2H), 8.25 (t, J=5.7 Hz, 1H); mp >200 (decomp.); MS (m/z): [M+H]+=459.

Workup

  1. customevaporated to dryness
  2. customthe residue is purified by PTLC (10% MeOH/DCM)

Sources & evidence

ORD record
ord-1efdfeee77034f14a3faa7fa6f6f9ceb
Source dataset
uspto-grants-2004_12
Patent number
US06828317B2

Reaction notes

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