HCID 178493272, compound → HCID 178493271, compound

HRID 630388Notes

Reaction equation

[OH:1][C:2]([C:35]1[S:36][CH:37]=[CH:38][CH:39]=1)([C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]([CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([CH2:27][OH:28])=[CH:21][C:20]=2[Cl:29])=[O:17])[CH3:13])[CH2:8][CH2:7]1)=[O:4]>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[OH:1][C:2]([C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)([C:35]1[S:36][CH:37]=[CH:38][CH:39]=1)[C:3]([O:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([N:12]([CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([CH:27]=[O:28])=[CH:21][C:20]=2[Cl:29])=[O:17])[CH3:13])[CH2:10][CH2:11]1)=[O:4]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of trans-4-((3-(2-chloro-4-(hydroxymethyl)-5-methoxyphenylamino)-3-oxopropyl)(methyl)amino)cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 42; 0.4 g, 0.68 mmol) in chloroform (8.1 mL) was added in portions manganese (IV) oxide (0.62 mg, 7.2 mmol). The heterogeneous mixture was stirred at 45° C. for 3 hours. The mixture was filtered and the solvent was removed under reduced pressure to give the title compound as a yellow solid (88%), which was used in the next step without further purification.

Workup

filtrationThe mixture was filtered
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-1b813d8016a14272b67639a1a601b5c0
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315463B2

Reaction notes

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