Methanol → HCID 71008354, compound

HRID 1845971Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]([CH:15]=1)=[N:13][C:12]([O:16][C@H:17]1[CH2:51][N:20]3[C:21](=[O:50])[C@@H:22]([NH:41][C:42]([C:44]4[CH:48]=[C:47]([CH3:49])[O:46][N:45]=4)=[O:43])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][C@@H:30]4[CH2:35][C@@:31]4([C:36]([O:38]CC)=[O:37])[NH:32][C:33](=[O:34])[C@@H:19]3[CH2:18]1)=[C:11]1[C:6]=2[CH:7]=[CH:8][CH:9]=[CH:10]1.CO.O.O.[OH-].[Li+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]([CH:15]=1)=[N:13][C:12]([O:16][C@H:17]1[CH2:51][N:20]3[C:21](=[O:50])[C@@H:22]([NH:41][C:42]([C:44]4[CH:48]=[C:47]([CH3:49])[O:46][N:45]=4)=[O:43])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][C@@H:30]4[CH2:35][C@@:31]4([C:36]([OH:38])=[O:37])[NH:32][C:33](=[O:34])[C@@H:19]3[CH2:18]1)=[C:11]1[C:6]=2[CH:7]=[CH:8][CH:9]=[CH:10]1

Participants

Conditions

Temperature: 40 °C

Procedure

(2R,6S,13aS,14aR,16aS,Z)-ethyl 2-(3-fluorophenanthridin-6-yloxy)-6-(5-methylisoxazole-3-carboxamido)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (846 mg, 1.21 mmol) was dissolved in tetrahydrofuran (6 mL), methanol (3 mL), and water (3 mL) and lithium hydroxide monohydrate (76 mg, 1.8 mmol) was added. The reaction mixture was heated at 40° C. for 4 h. The mixture was cooled to rt and partitioned between 2 N HCl and dichloromethane. The organic layer was concentrated under reduced pressure and then azeoptroped with toluene and chloroform to provide the title compound (0.812 g, quantitative yield) as a colorless solid that was used without further purification.

Workup

temperatureThe mixture was cooled to rt
custompartitioned between 2 N HCl and dichloromethane
concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-13d88eddd49e42da9b05f76dc421c015
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08951964B2

Reaction notes

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