Dichloromethane → HCID 58169901, compound

HRID 384028Notes

Reaction equation

HRID 384028 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:40])[C:16]([N:18]2[CH2:31][CH2:30][C@:21]3([NH:25][C@H:24]([C:26]([O:28][CH3:29])=[O:27])[CH2:23][CH2:22]3)[CH2:20][C@@H:19]2[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=2[CH3:39])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.ClCCl.[C:46]([O-:49])(O)=[O:47].[Na+]>>[F:42][C:2]([F:1])([F:41])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:40])[C:16]([N:18]2[CH2:31][CH2:30][C@:21]3([N:25]([C:46]([O:49][C:3]([CH3:4])([CH3:8])[CH3:2])=[O:47])[C@H:24]([C:26]([O:28][CH3:29])=[O:27])[CH2:23][CH2:22]3)[CH2:20][C@@H:19]2[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=2[CH3:39])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 58169846HCID 58169846, compound2×

Product 1

HCID 58169901HCID 58169901, compoundYield 87.7%

Procedure

To a solution of methyl(2S,5S,7R)-8-{[{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-7-(4-fluoro-2-methylphenyl)-1,8-diazaspiro[4.5]decane-2-carboxylate (Intermediate 13, 12 g, 19.88 mmol) in dry Dichloromethane (DCM) (80 ml) TEA (4.16 ml, 29.8 mmol) and then BOC-Anhydride (5.54 ml, 23.86 mmol) were added and the reaction mixture was stirred overnight at r.t. The reaction was diluted with NaHCO3 sat. sol. (400 ml) and two phases were separated. The organic layer was dried (Na2SO4), filtered and evaporated in vacuo and the residue was purified by flash chromatography on silica gel using a Biotage 65i as column and Cyclohexane to Cyclohexane/Ethyl acetate 7:3 as eluent affording the title compound (12.2 g, 17.43 mmol, y=87.7%).

Workup

  1. customwere separated
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customthe residue was purified by flash chromatography on silica gel using a Biotage 65i as column and Cyclohexane to Cyclohexane/Ethyl acetate 7:3 as eluent

Sources & evidence

ORD record
ord-0fbf79200d7847978cccb9bf3a34a092
Source dataset
uspto-grants-2013_02
Patent number
US08367692B2

Reaction notes

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