HCID 86727512, compound → HCID 86727511, compound

HRID 519126Notes

Reaction equation

HRID 519126 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([CH3:34])([C:12]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[C:28]([F:31])([F:30])[F:29])[O:24][CH2:23][C:22]2[N:17]3[C@H:18]([CH3:33])[C:19](=[O:32])[NH:20][N:21]=2)=[CH2:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([CH3:34])([CH:12]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[C:28]([F:30])([F:29])[F:31])[O:24][CH2:23][C:22]2[N:17]3[C@H:18]([CH3:33])[C:19](=[O:32])[NH:20][N:21]=2)[CH3:13])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86727512HCID 86727512, compound

Product 1

HCID 86727511HCID 86727511, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-methyl-3-[1-((R)-4-methyl-3-oxo-7-trifluoromethyl-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-vinyl]-azetidine-1-carboxylic acid tert-butyl ester (enantiomer 2, 0.089 g, 0.185 mmol) in MeOH (12 mL) was added 10% Pd/C (0.039 g, 0.037 mmol) and the reaction mixture was stirred under H2 at ambient temperature for 1 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give 3-methyl-3-[1-((R)-4-methyl-3-oxo-7-trifluoromethyl-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-ethyl]-azetidine-1-carboxylic acid tert-butyl ester (0.084 g, 94%). LC/MS (Table 1, Method 25) Rt=0.934 min; MS m/z: 427 [M+H−56]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-177d39ba6bad4dcba1397908a0100709
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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