Sodium Hydroxide → 3-(2-o-Tolylamino-benzoxazol-6-yl)propanoic acid

HRID 987528Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of ethyl 3-(2-o-tolylamino-benzoxazol-6-yl)propanoate (Reference Example 15) in methanol (50 ml) was treated with aqueous sodium hydroxide (5 ml, 1M). After stirring at 40° C. for 2 hours the mixture was evaporated to low volume and partitioned between ethyl acetate (50 ml) and water (50 ml). The aqueous phase was separated and acidified with aqueous hydrochloric acid (10 ml, 1M). The resulting precipitate was dried at 60° C. to give the title compound (1.1 g).

Workup

customwas evaporated to low volume
custompartitioned between ethyl acetate (50 ml) and water (50 ml)
customThe aqueous phase was separated
customThe resulting precipitate was dried at 60° C.

Sources & evidence

ORD record: ord-b38d8f145dad4f319171d8ce9861c74b
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632814B1

Reaction notes

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