Methylamine ethanol → HCID 59201385, compound

HRID 451910Notes

Reaction equation

HRID 451910 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:43])[CH2:9][C@@H:10]([NH:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][C@@H:23]([C@H:27]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=2)[O:28][CH2:29][CH2:30][CH2:31][C:32]([O:34]C)=O)[CH2:22]1)=[O:20])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:44][NH2:45].C(O)C>>[Cl:42][C:38]1[CH:37]=[C:36]([C@H:27]([O:28][CH2:29][CH2:30][CH2:31][C:32]([NH:45][CH3:44])=[O:34])[C@@H:23]2[CH2:24][CH2:25][CH2:26][N:21]([C:19]([NH:18][C@@H:10]([CH2:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]3)[CH2:9][N:8]([CH3:43])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:20])[CH2:22]2)[CH:41]=[CH:40][CH:39]=1

Participants

3

Reactant 2

HCID 22028356Methylamine ethanolHCID 59201638HCID 59201638, compound

Product 1

HCID 59201385HCID 59201385, compoundYield 71%

Procedure

methyl 4-((R)—((R)-1-((S)-1-(tert-butoxycarbonyl(methyl)amino)-3-cyclohexylpropan-2-ylcarbamoyl)piperidin-3-yl)(3-chlorophenyl)methoxy)butanoate (70 mg, 0.11 mmol) was dissolved in the CH3NH2/C2H5OH (20 mL), which was stirred at rt overnight. After the reaction was completed, the solvent was removed in vacuo. The product was purified via preparative TLC to afford tert-butyl (S)-2-((R)-3-((R)-(3-chlorophenyl)(4-(methylamino)-4-oxobutoxy)methyl)piperidine-1-carboxamido)-3-cyclohexylpropyl(methyl)carbamate (50 mg, 71% yield), which was used immediately in the next step.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe product was purified via preparative TLC

Sources & evidence

ORD record
ord-a60209851ec745fa843f34139bf1b488
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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