Sodium Hydroxide → 4-[4-(Azetidine-1-carbonyl)-phenoxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid

HRID 1177098Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

Aqueous NaOH (3 N, 2.1 mL, 6.3 mmol) was added to a solution of 4-[4-(azetidine-1-carbonyl)-phenoxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (35b) (802 mg, 2.10 mmol) in 10 mL CH3OH. The mixture was heated to 60° C. for 3 hr, concentrated, diluted with H2O (60 mL) and acidified with 1N aqueous HCl to pH˜1. The aqueous phase was extracted with CH2Cl2 (60 mL), dried with MgSO4 and concentrated to give a white solid (598 mg, 74% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.99 (s, 1 H) 7.67 (d, J=7.33 Hz, 2 H) 7.02-7.10 (m, 3 H) 6.99 (s, 1 H) 4.32 (s, 2 H) 4.03 (s, 2 H) 2.89 (s, 2 H) 2.21-2.30 (m, 2 H) 1.42 (s, 6 H); LCMS for C21H21NO5 m/z 468.00 (M+H)+.

Workup

concentrationconcentrated
additiondiluted with H2O (60 mL)
extractionThe aqueous phase was extracted with CH2Cl2 (60 mL)
dry with materialdried with MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-4358c1da825445649a16e2c4b641dd13
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842713B2

Reaction notes

Loading…