Triethylamine → Methyl 4-({[4-({(tert-butoxycarbonyl)[(1r)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidin-1-yl]carbonyl}amino)-3-chlorobenzoate

HRID 1691722

Reaction equation

HRID 1691722 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH:13]([CH2:14][N:15]([C@@H:23]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[CH3:24])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:35][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][C:45]=1[NH:46][C:47](OC1C=CC([N+]([O-])=O)=CC=1)=[O:48])[C:39]([O:41][CH3:42])=[O:40].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C1COCC1>[C:18]([O:17][C:16]([N:15]([CH2:14][CH:13]1[CH2:12][CH2:11][N:10]([C:47]([NH:46][C:45]2[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][C:36]=2[Cl:35])=[O:48])[CH2:9][CH:8]1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[C@@H:23]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)[CH3:24])=[O:22])([CH3:19])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 59178728HCID 59178728, compoundHCID 59178754Methyl 3-chloro-4-{[(4-nitrophenoxy)carbonyl]amino}benzoate

Product 1

HCID 66906552Methyl 4-({[4-({(tert-butoxycarbonyl)[(1r)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidin-1-yl]carbonyl}amino)-3-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 231 mg of tert-butyl {[3-(3-fluorophenyl)piperidin-4-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate and 210 mg of methyl 3-chloro-4-{[(4-nitrophenoxy)carbonyl]amino}benzoate in 4.0 mL of THF was added 0.139 mL of triethylamine at room temperature, followed by stirring overnight. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 394 mg of a pale yellow foamy substance of methyl 4-({[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidin-1-yl]carbonyl}amino)-3-chlorobenzoate as a crude product. ESI+: 674

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine in this order
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f9c2c5d65e7b44789995d72a5df3a2ce
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Linked notes

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