Trifluoroacetic acid → 5-Amino-5-methyl-hex-2-enoic acid (1-{[2-(2-fluorophenyl)-1-methylcarbamoylethyl]methylcarbamoyl}2-(2-naphthyl)ethyl)methylamide

HRID 495845Notes

Reaction equation

HRID 495845 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:46])([CH3:45])[CH2:9][CH:10]=[CH:11][C:12](=[O:44])[N:13]([CH:15]([C:27](=[O:43])[N:28]([CH:30]([C:39](=[O:42])[NH:40][CH3:41])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[F:38])[CH3:29])[CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1)[CH3:14])(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[F:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:31][CH:30]([N:28]([CH3:29])[C:27]([CH:15]([N:13]([CH3:14])[C:12](=[O:44])[CH:11]=[CH:10][CH2:9][C:8]([NH2:7])([CH3:46])[CH3:45])[CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1)=[O:43])[C:39](=[O:42])[NH:40][CH3:41]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10791Sodium SesquicarbonateHCID 516892Sodium BicarbonateHCID 53791932{4-[(1-{[2-(2-Fluorophenyl)-1-methylcarbamoylethyl]methylcarbamoyl}-2-(2-naphthyl)ethyl)methylcarbamoyl]-1,1-dimethyl-but-3-enyl}carbamic acid tert-butyl ester

Product 1

HCID 537599165-Amino-5-methyl-hex-2-enoic acid (1-{[2-(2-fluorophenyl)-1-methylcarbamoylethyl]methylcarbamoyl}2-(2-naphthyl)ethyl)methylamideYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

{4-[(1-{[2-(2-Fluorophenyl)-1-methylcarbamoylethyl]methylcarbamoyl}2-(2-naphthyl)ethyl)methylcarbamoyl]-1,1-dimethyl-but-3-enyl}carbamic acid tert-butyl ester (0.36 g; 0.557 mmol) was dissolved in methylene chloride (3 ml). Trifluoro acetic acid (3 ml) was added and the reaction mixture was stirred 5 min at room temperature. Methylene chloride (25 ml), sodium hydrogen carbonate/sodium carbonate (3 ml) and sodium hydrogen carbonate (s) was added until pH=8. The organic phase was dried (magnesium sulfate) and the solvent was removed in vacuo. The residue was lyophylised to afford 0.237 g of the title compound.

Workup

  1. dry with materialThe organic phase was dried (magnesium sulfate)
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-420d309a64f94df0a55893ccd55cc46f
Source dataset
uspto-grants-2005_09
Patent number
US06939880B2

Reaction notes

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