Sodium Acetate → HCID 86602135, compound

HRID 1726279Notes

Reaction equation

HRID 1726279 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:32][C:33]2[CH:37]=[CH:36][S:35][CH:34]=2)[CH:11]2[CH2:16][CH2:15][N:14]([C@H:17]([CH3:31])[CH2:18][CH2:19][NH:20][C:21]([C:23]3[C:24]([CH3:30])=[N:25][CH:26]=[N:27][C:28]=3[CH3:29])=[O:22])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[O:39]([NH2:41])[CH3:40].CC([O-])=O.[Na+]>CO>[CH3:40][O:39][N:41]=[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]([CH2:32][C:33]2[CH:37]=[CH:36][S:35][CH:34]=2)[CH:11]2[CH2:16][CH2:15][N:14]([C@H:17]([CH3:31])[CH2:18][CH2:19][NH:20][C:21]([C:23]3[C:24]([CH3:30])=[N:25][CH:26]=[N:27][C:28]=3[CH3:29])=[O:22])[CH2:13][CH2:12]2)=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 57563012HCID 57563012, compound

Product 1

HCID 86602135HCID 86602135, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of COMPOUND 293 in MeOH (3 mL) were added methoxylamine hydrochloride (15 mg, 0.18 mmol) followed by NaOAc (14 mg, 0.17 mmol) and the mixture was stirred at room temperature overnight to afford COMPOUND 294 as a clear oil (31 mg, 82%) after work-up and purification. 1H NMR (CDCl3) δ 0.95-1.17 (m, 2H), 1.02 (d, 3H, J=6.6 Hz), 1.52-1.58 (m, 1H), 1.74-1.79 (m, 3H), 2.14 (s, 3H), 2.17 (t, 1H, J=11.7 Hz), 2.52 (s, 6H), 2.57 (t, 1H, J=11.4 Hz), 2.73-2.89 (m, 3H), 3.28-3.36 (m, 1H), 3.59-3.68 (m, 1H), 3.88 (s, 3H), 3.94 (s, 3H), 6.60 (d, 2H, J=9.0 Hz), 6.98-7.03 (m, 2H), 7.28 (dd, 1H, J=4.8, 3.0 Hz), 7.45 (d, 2H, J=9.0 Hz), 8.71 (br s, 1H), 8.89 (s, 1H). ES-MS m/z 549 (M+H).

Sources & evidence

ORD record
ord-50c20b8b12614181b439390cc9ac97d2
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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