Acetic Acid → HCID 58232113, compound

HRID 2095585Notes

Reaction equation

HRID 2095585 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:12]2[CH:18]=[CH:17][C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH2:22][C:23]([N:25]3[CH2:32][CH2:31][C:28]4([CH2:30][CH2:29]4)[C@H:27]([OH:33])[CH2:26]3)=[O:24])[CH2:14][C@H:13]2[CH3:34])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C(O)(=O)C>CO.O=[Pt]=O.O=[Pt]=O.[H][H]>[Cl:1][C:2]1[CH:3]=[C:4]([N:12]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH2:22][C:23]([N:25]3[CH2:32][CH2:31][C:28]4([CH2:29][CH2:30]4)[C@H:27]([OH:33])[CH2:26]3)=[O:24])[CH2:14][C@H:13]2[CH3:34])[CH:5]=[CH:6][C:7]=1[C:8]([F:10])([F:9])[F:11]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 58232178(R)-1-(3-chloro-4-trifluoromethyl-phenyl)-4-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-2-methyl-1,2,3,4-tetrahydro-[1,4]diazepin-5-one

Product 1

HCID 58232113HCID 58232113, compoundYield 113.6%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 178506448HCID 178506448, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.066 g (0.1 mmol) of (R)-1-(3-chloro-4-trifluoromethyl-phenyl)-4-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-2-methyl-1,2,3,4-tetrahydro-[1,4]diazepin-5-one (61% ds) (example 65) in 2 ml MeOH was treated with 0.007 g of PtO2 and was stirred over H2-atmosphere for 2 days. After filtration and evaporation, the crude compound was again hydrogenated in 2 ml of MeOH and 0.007 ml (0.1 mmol) of acetic acid with 0.007 g of PtO2/H2 over night. After filtration and evaporation, the residue was reevaporated (3 times) with toluene and the solvent was removed under vacuum to give 0.057 g (86%) of the titled compound as white foam. MS: 502.21 (MH+, Cl).

Workup

  1. filtrationAfter filtration and evaporation
  2. filtrationAfter filtration and evaporation
  3. customthe residue was reevaporated (3 times) with toluene
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-b98a333875e24bd5a6eadbc366057711
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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