HCID 58169881, compound → HCID 58169871, compound

HRID 472690Notes

Reaction equation

HRID 472690 reaction equation
[F:1][C:2]([F:53])([F:52])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:51])[C:16]([N:18]2[CH2:42][CH2:41][C@:21]3([N:25](C(OCC4C=CC=CC=4)=O)[C:24](=[O:36])[CH:23]([C:37]([O:39][CH3:40])=[O:38])[CH2:22]3)[CH2:20][C@@H:19]2[C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][C:44]=2[CH3:50])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>CO.[Pd]>[F:53][C:2]([F:1])([F:52])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:51])[C:16]([N:18]2[CH2:42][CH2:41][C@:21]3([NH:25][C:24](=[O:36])[CH:23]([C:37]([O:39][CH3:40])=[O:38])[CH2:22]3)[CH2:20][C@@H:19]2[C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][C:44]=2[CH3:50])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

Participants

4

Reactant 1

HCID 58169881HCID 58169881, compound2×

Product 1

HCID 58169871HCID 58169871, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-methyl 1-(phenylmethyl) (5S,7R)-8-{[{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-7-(4-fluoro-2-methylphenyl)-2-oxo-1,8-diazaspiro[4.5]decane-1,3-dicarboxylate (Intermediate 34, 78 mg) was dissolved in Methanol (3 ml), Pd/C (8.83 mg, 8.30 μmol) was added and the suspension was left stirring at rt, under a H2 atmosphere (1 atm), for 1 hr. The Pd was filtered out and the solvent was removed obtaining the title compound (60 mg); UPLC: Rt=0.82 mins, m/z=618 [M+H]+.

Workup

  1. waitthe suspension was left
  2. filtrationThe Pd was filtered out
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-b68010b547d6421384b89a6f9a8a8410
Source dataset
uspto-grants-2014_01
Patent number
US08633214B2

Reaction notes

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