Sodium Acetate → HCID 76566971, compound

HRID 1726264Notes

Reaction equation

HRID 1726264 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH:19]3[CH2:24][CH2:23][N:22]([CH:25]([CH3:39])[CH2:26][CH2:27][NH:28][C:29]([C:31]4[C:32]([CH3:38])=[N:33][CH:34]=[N:35][C:36]=4[CH3:37])=[O:30])[CH2:21][CH2:20]3)[O:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11]2)=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[O:41]([NH2:43])[CH3:42].CC([O-])=O.[Na+]>CO>[CH3:42][O:41][N:43]=[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2([CH:19]3[CH2:20][CH2:21][N:22]([CH:25]([CH3:39])[CH2:26][CH2:27][NH:28][C:29]([C:31]4[C:32]([CH3:38])=[N:33][CH:34]=[N:35][C:36]=4[CH3:37])=[O:30])[CH2:23][CH2:24]3)[O:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[O:14]2)=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 57563137HCID 57563137, compound

Product 1

HCID 76566971HCID 76566971, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of COMPOUND 282 (47 mg, 0.089 mmol) in MeOH (4 mL) was added methoxylamine hydrochloride (19 mg, 0.22 mmol) and NaOAc (21 mg, 0.25 mmol) and the mixture was stirred at room temperature overnight. Standard work-up and purification afforded COMPOUND 283 as a white solid (38 mg, 75%). 1H NMR (CDCl3) δ 0.76-0.81 (m, 1H), 0.94 (d, 3H, J=6.6 Hz), 1.01-1.06 (m, 1H), 1.45-1.75 (m, 4H), 1.88-1.96 (m, 2H), 2.19 (s, 3H), 2.37 (t, 1H, J=10.7 Hz), 2.51 (s, 6H), 2.66-2.82 (m, 3H), 3.22-3.30 (m, 1H), 3.84-3.94 (m, 1H), 3.98 (s, 3H), 6.75-6.78 (m, 2H), 6.84-6.87 (m, 1H), 6.93-6.96 (m, 1H), 7.37 (d, 2H, J=8.4 Hz), 7.61 (d, 2H, J=8.4 Hz), 8.82-8.83 (m, 1H), 9.08 (s, 1H). 13C NMR (CDCl3) δ 12.63, 13.18, 21.54, 21.89, 25.60, 26.25, 30.62, 40.22, 43.57, 45.17, 52.24, 60.78, 61.77, 62.00, 108.53, 108.63, 117.87, 121.39, 125.35, 125.69, 125.79, 127.78, 130.82, 137.07, 140.48, 147.05, 147.16, 154.18, 157.68, 162.88, 166.51. ES-MS m/z 558 (M+H). Anal. Calcd. for C32H39N5O4.0.15CH2Cl2: C, 67.70; H, 6.94; N, 12.28. Found: C, 67.71; H, 7.06; N, 12.16.

Workup

  1. customStandard work-up and purification

Sources & evidence

ORD record
ord-bad98bbae4864df888e800cd38147a0e
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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