Methanol → HCID 68008615, compound

HRID 1429082Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([OH:28])[CH2:27][C@H:21]2[C:20](=[O:29])[NH:19][C@:18]2([C:31]([O:33]CC)=[O:32])[CH2:30][C@H:17]2[CH2:16][C:15]([F:37])([F:36])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.CO.O.[OH-].[Li+]>CC#N.Cl.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([OH:28])[CH2:27][C@H:21]2[C:20](=[O:29])[NH:19][C@:18]2([C:31]([OH:33])=[O:32])[CH2:30][C@H:17]2[CH2:16][C:15]([F:37])([F:36])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

To (2R,6S,13aS,14aR,16aS)-ethyl 6-(tert-butoxycarbonylamino)-12,12-difluoro-2-hydroxy-5,16-dioxooctadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (Example 7i, 900 mg, 1.693 mmol) was added tetrahydrofuran (5.6 ml), methanol (2.80 ml) and water (2.80 ml). Lithium hydroxide monohydrate (145.44 mg, 3.47 mmol) was added at room temperature, and the reaction mixture was stirred at 40° C. for 16 h. The reaction mixture was diluted with CH3CN and neutralized with HCl (2 N, 1.7 ml). The mixture was concentrated under reduced pressure and azeotroped with chloroform followed by ethyl acetate and dried overnight at reduced pressure to provide the title compound (850 mg, quantitative yield). This material was utilized in subsequent reactions without additional purification.

Workup

concentrationThe mixture was concentrated under reduced pressure
customazeotroped with chloroform
customdried overnight at reduced pressure

Sources & evidence

ORD record: ord-c4f3dde632c5490bbe6b3135b7da677b
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937041B2

Reaction notes

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