Sodium Hydroxide → HCID 59560311, compound

HRID 1643581Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 59559927HCID 59559927, compound

Product 1

HCID 59560311HCID 59560311, compoundYield 22%

Procedure

NaOH (110 uL, 0.1 mmol, 3N aqueous solution) was added to a solution of 6-[(4-benzyloxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carbonyl)-amino]-nicotinic acid methyl ester (77c) (48 mg, 0.11 mol). The reaction mixture was stirred at room temperature overnight. The mixture was concentrated and purified by reverse phase chromatograph to give a white solid (10 mg, 22% yield). 1H NMR (400 MHz, CD3OD) δ 8.93 (s, 1 H) 8.31-8.41 (m, 1 H) 8.21-8.31 (m, 1 H) 7.47-7.54 (m, 2 H) 7.42 (t, J=7.33 Hz, 1 H) 7.35 (t, J=7.07 Hz, 1 H) 7.23 (s, 1 H) 7.00 (s, 1 H) 5.24 (s, 2 H) 3.06 (s, 2 H) 1.51 (s, 6 H); LCMS for C24H22N2O5 m/z 419.00 (M+H)+.

Workup

concentrationThe mixture was concentrated
custompurified by reverse phase chromatograph

Sources & evidence

ORD record: ord-74067c00784540b1bff4db0470cef875
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119624B2

Reaction notes

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