m-Chloroperbenzoic acid → Amino(1,3-dihydrobenzo[c]thien-4-yl)acetic acid

HRID 1856491

Reaction equation

C([O:5][C:6]([C:8]([NH2:21])([C:12]1[C:20]2[CH2:19][S:18][CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)C(O)=O)=[O:7])(C)(C)C.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)(Cl)Cl>[NH2:21][CH:8]([C:12]1[C:20]2[CH2:19][S:18][CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)[C:6]([OH:7])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

α-(tert-Butoxycarbonyl)amino(1,3-dihydrobenzo[c]thien-4-yl)acetic acid (0.05 m) is added to chloroform and the mixture cooled to about 0° C. Over a period of about 2.5 hours, 0.12 moles of m-chloroperbenzoic acid dissolved in chloroform is added to the mixture maintained at 0° C. When the addition of the m-chloroperbenzoic acid is complete, the temperature of the mixture is raised to about 20° to 25° C. from about 0° C. and stirred for about 18 hours, chilled to 0° C. to precipitate the m-chlorobenzoic acid which is filtered from the solution. Removal of a portion of the chloroform results in the precipitation of Amino(1,3-dihydrobenzo[c]thien-4-yl)acetic acid, 2-oxide

Workup

additionis added to the mixture
temperaturemaintained at 0° C
temperaturethe temperature of the mixture is raised to about 20° to 25° C. from about 0° C.
temperaturechilled to 0° C.
customto precipitate the m-chlorobenzoic acid which
filtrationis filtered from the solution
customRemoval of a portion of the chloroform

Sources & evidence

ORD record: ord-0393858ba19e462bab5296743c545fbc
Source dataset: uspto-grants-1980_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04219648

Linked notes

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