Hydrochloric Acid → HCID 57277500, compound

HRID 1596353Notes

Reaction equation

[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:10]([CH2:12][N:13]1[C:19]3[C:20]([Cl:24])=[CH:21][CH:22]=[CH:23][C:18]=3[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])=[N:16][CH:15]([NH:32]C(OC(C)(C)C)=O)[C:14]1=[O:40])=[O:11])[CH2:2]2.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:32][CH:15]1[N:16]=[C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[N:13]([CH2:12][C:10]([N:3]2[CH2:4][CH:5]3[CH2:8][CH2:9][CH:1]([CH2:7][CH2:6]3)[CH2:2]2)=[O:11])[C:14]1=[O:40]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of (3RS)-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-9-chloro-2,3-dihydro-5-(2-fluorophenyl)-3-tert-butoxycarbonylamino-1H-1,4-benzodiazepin-2-one (660 mg) and 4N aqueous hydrochloric acid in ethyl acetate (3 ml) was stirred at 0° C. for 5.5 hours. A saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the reaction mixture. The separated organic layer was washed with water and brine, and then dried over sodium sulfate. The solvent was evaporated in vacuo to afford (3RS)-3-amino-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-9-chloro-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one (549.0 mg) as a crystalline powder.

Workup

washThe separated organic layer was washed with water and brine
dry with materialdried over sodium sulfate
customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-c22282739818413a845abc55f4cf6971
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291452B1

Reaction notes

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