Hydrochloric Acid → 6-[(R)-1-(4-fluoro-phenyl)-ethylcarbamoyl]-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid

HRID 926362Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 6-[(R)-1-(4-fluoro-phenyl)-ethylcarbamoyl]-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ethyl ester (9.0 g, 25 mmol) in methanol (38 ml) was added 2 N aqueous sodium hydroxide (38 ml, 76 mmol). The mixture was stirred for 1 h at 60° C., then cooled down to 25° C. acidified with excess 10 M aqueous hydrochloric acid. After extraction (3 times with dichloromethane), the combined organic layers were dried over sodium sulfate and the solvents evaporated to give 7.2 g (85%) 6-[(R)-1-(4-fluoro-phenyl)-ethylcarbamoyl]-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid as a white solid. LC/MS (method 4): Rt=1.11 min; m/z=333.06 (M+H+).

Workup

temperaturecooled down to 25° C.
extractionAfter extraction (3 times with dichloromethane)
dry with materialthe combined organic layers were dried over sodium sulfate
customthe solvents evaporated

Sources & evidence

ORD record: ord-07f37a8e0fde4608a66543864a213905
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284333B2

Reaction notes

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