Sodium Hydroxide → [1-(3,4-Dimethoxy-benzyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-phenyl-acetic acid

HRID 458785Notes

Reaction equation

C[O:2][C:3](=[O:37])[CH:4]([N:11]1[CH2:17][CH2:16][CH2:15][C:14]2[CH:18]=[C:19]([O:24][CH3:25])[C:20]([O:22][CH3:23])=[CH:21][C:13]=2[CH:12]1[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O1CCOCC1>[CH3:36][O:35][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[O:33][CH3:34])[CH2:26][CH:12]1[C:13]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[CH:18][C:14]=2[CH2:15][CH2:16][CH2:17][N:11]1[CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:3]([OH:37])=[O:2]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of [1-(3,4-dimethoxy-benzyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-phenyl-acetic acid methyl ester (1.17 g, 2.31 mmol), in MeOH (9 ml) and dioxane (12 ml), was added dropwise aqueous NaOH 2N (11 ml, 22 mmol). The resulting yellow homogeneous mixture was then stirred at 45° C. for 8 h. The reaction mixture was then concentrated in vacuo and washed with Et2O (5 ml). The aqueous phase was acidified (pH=1) with HCl 2N and extracted three times with CH2Cl2. The combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give the titled carboxylic acid (1.14 g, 2.31 mmol, 100%) as a beige solid (mixture of diastereoisomers).

Workup

concentrationThe reaction mixture was then concentrated in vacuo
washwashed with Et2O (5 ml)
extractionextracted three times with CH2Cl2
dry with materialThe combined organic phases were dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated
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Sources & evidence

ORD record: ord-2a889e7e93c249f1ba584d81f19f4a7f
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192950B2

Reaction notes

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