Water → HCID 58169880, compound

HRID 472688Notes

Reaction equation

HRID 472688 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[F:12][C:13]([F:60])([F:59])[C:14]1[CH:15]=[C:16]([C@H:24]([N:26]([CH3:58])[C:27]([N:29]2[CH2:49][CH2:48][C@:32]3([N:36]([C:37]([O:39][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[O:38])[CH:35]([OH:47])[CH2:34][CH2:33]3)[CH2:31][C@@H:30]2[C:50]2[CH:55]=[CH:54][C:53]([F:56])=[CH:52][C:51]=2[CH3:57])=[O:28])[CH3:25])[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1.O>C(Cl)Cl>[F:60][C:13]([F:12])([F:59])[C:14]1[CH:15]=[C:16]([C@H:24]([N:26]([CH3:58])[C:27]([N:29]2[CH2:49][CH2:48][C@:32]3([N:36]([C:37]([O:39][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[O:38])[C:35](=[O:47])[CH2:34][CH2:33]3)[CH2:31][C@@H:30]2[C:50]2[CH:55]=[CH:54][C:53]([F:56])=[CH:52][C:51]=2[CH3:57])=[O:28])[CH3:25])[CH:17]=[C:18]([C:20]([F:23])([F:21])[F:22])[CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 58169907HCID 58169907, compound2×HCID 178418287HCID 178418287, compound2×

Product 1

HCID 58169880HCID 58169880, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of Pyridinium chlorochromate (PCC) (66.5 mg, 0.307 mmol) in DCM (2 ml) was added a solution of phenylmethyl (5S,7R)-8-{[{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-7-(4-fluoro-2-methylphenyl)-2-hydroxy-1,8-diazaspiro[4.5]decane-1-carboxylate (Intermediate 32, 107 mg) in DCM (2 ml) and the reaction mixture was left stirring at it for 1 hr. Further pyridinium chlorochromate (PCC) (66.5 mg, 0.307 mmol) was added and the reaction mixture was left stirring overnight. To the mixture were added H2O and further DCM. The two phases were separated and the organic one was washed two times with water and filtered through a phase separator tube. The crude obtained after evaporation was purified by Flash Chromatography (20 g cartridge; eluting from 2:1 to 1:1 Cy:EtOAc). Relevant fractions were collected and the solvent removed in vacuo obtaining the title compound (86 mg) as a white solid; UPLC: Rt=0.95 mins, m/z=694 [M+H]+.

Workup

  1. waitthe reaction mixture was left
  2. waitthe reaction mixture was left
  3. stirringstirring overnight
  4. customThe two phases were separated
  5. washthe organic one was washed two times with water
  6. filtrationfiltered through a phase separator tube
  7. customThe crude obtained
  8. customafter evaporation
  9. customwas purified by Flash Chromatography (20 g cartridge; eluting from 2:1 to 1:1 Cy:EtOAc)
  10. customRelevant fractions were collected
  11. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0218482fec1d40d0abe3fbf9d6fc1c03
Source dataset
uspto-grants-2014_01
Patent number
US08633214B2

Reaction notes

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