Isopropanol → Turofexorate isopropyl

HRID 37976Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[F:31])[C:5]([N:7]1[CH2:20][C:19]([CH3:22])([CH3:21])[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:8]1)=[O:6].[CH:32](O)(C)C>>[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[F:31])[C:5]([N:7]1[CH2:20][C:19]([CH3:22])([CH3:21])[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[C:9]([C:23]([O:25][CH:26]([CH3:32])[CH3:27])=[O:24])=[CH:8]1)=[O:6]

Participants

Reactant 2

HCID 3776Isopropanol

HCID 57817588HCID 57817588, compound

Product 1

HCID 10026128Turofexorate isopropyl

Procedure

Ethyl 3-(3,4-difluorobenzoyl)-1,1-dimethyl-1,2,3,4,5,6-hexahydro-azepino[4,5-b]indole-5-carboxylate was saponified, converted to the corresponding isopropyl ester using CU and isopropanol, and then oxidized as described previously in Step D of Example 63 to give the title compound; 1H-NMR (DMSO-d6): δ 10.83 (1H, s), 7.76 (1H, d), 7.71 (1H, app t), 7.64 (1H, s), 7.52-7.61 (2H, m), 7.40 (1H, m), 7.08 (1H, app t), 6.98 (1H, app t), 5.05 (1H, sept), 1.52 (6H, s), 1.18 (6H, d); MS (ESI): 439 (MH+).

Sources & evidence

ORD record: ord-e0443b3f00e44abd9411ee1e424aff8e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524704B2

Reaction notes

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