HCID 136396902, compound → HCID 136396968, compound

HRID 2110588Notes

Reaction equation

HRID 2110588 reaction equation
[C:1]([N:4]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:5]1([CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([N:26]([S:30]([CH3:33])(=[O:32])=[O:31])C(=O)C)=[CH:25][C:19]=3[S:18](=[O:35])(=[O:34])[N:17]=2)[C:6]1=[O:36])(=[O:3])[CH3:2]>CO.C([O-])(O)=O.[Na+]>[CH2:43]([O:42][N:4]([C:5]1([CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:25][C:19]=3[S:18](=[O:34])(=[O:35])[N:17]=2)[C:6]1=[O:36])[C:1](=[O:3])[CH3:2])[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

4

Reactant 1

HCID 136396902HCID 136396902, compound

Product 1

HCID 136396968HCID 136396968, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of Example 24A (16 mg, 0.023 mmol) in methanol (0.4 mL) and 1N NaHCO3 (0.12 mL) was stirred at 25° C. for 1 h. The solution was concentrated in vacuo. Column chromatography on silica (5% methanol/dichloromethane) afforded the title compound (12 mg, 80%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.31-0.55 (m, 1H), 0.64 (dd, J=15.07, 6.62 Hz, 6H), 0.93-1.10 (m, 1H), 1.22-1.37 (m, 1H), 2.08 (s, 3H) 2.18-2.42 (m, 2H), 3.04 (s, 3H), 5.16-5.41 (m, 2H), 7.26-7.65 (m, 11H), 8.06 (d, 1H), 10.11 (s, 1H), 14.24 (br. s, 1H); MS m/z 666.4 (M+H)+.

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-66b458c4d72447f69c7f41c604dd1b67
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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