Sodium Hydroxide → HCID 67170581, compound

HRID 1475734Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

630 mg of 2-[4-methoxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid methyl ester was dissolved in 10 ml of methanol, and 2.2 ml of a 1 N solution of sodium hydroxide in water were added at room temperature. The mixture was stirred at 40° C. for 5 h, then another 1.1 ml of a 1 N solution of sodium hydroxide in water were added and the mixture stirred at 40° C. for another 4 h. The mixture was then diluted with 40 ml of water, the methanol was evaporated, the pH adjusted to 2 and the mixture stirred at room temperature of 1 h. The precipitated product was filtered off and dried in vacuo to yield 400 mg of 2-[4-methoxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid as a racemic mixture of (1R,2S,4S)-2-[4-methoxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid and (1S,2R,4R)-2-[4-methoxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid.

Workup

stirringthe mixture stirred at 40° C. for another 4 h
customthe methanol was evaporated
stirringthe mixture stirred at room temperature of 1 h
filtrationThe precipitated product was filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-06c03970d4cb4f9ebc72fc054e11cd99
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018383B2

Reaction notes

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