Trifluoroacetic acid → (R)-2-amino-1-(3-cyclohexyl-3-pentylazetidin-1-yl)-3-(4-methoxyphenyl)propan-1-one

HRID 540403Notes

Reaction equation

HRID 540403 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C@H:15]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)[C:16]([N:18]1[CH2:21][C:20]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19]1)=[O:17])(C)(C)C>ClCCl>[NH2:14][C@H:15]([CH2:33][C:34]1[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=1)[C:16]([N:18]1[CH2:21][C:20]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19]1)=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67295580tert-butyl[(R)-2-(3-cyclohexyl-3-pentylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]carbamate

Product 1

HCID 66988216(R)-2-amino-1-(3-cyclohexyl-3-pentylazetidin-1-yl)-3-(4-methoxyphenyl)propan-1-oneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.5 ml of trifluoroacetic acid are added, at 0° C., to 0.48 g (0.99 mmol) of tert-butyl[(R)-2-(3-cyclohexyl-3-pentylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]carbamate dissolved in 10 ml of dichloromethane. After 2 hours, the solvents are evaporated off. The residue is taken up in dichloromethane and washed with 1N sodium hydroxide. The organic phases are combined, dried over MgSO4, filtered and concentrated. 327 mg of (R)-2-amino-1-(3-cyclohexyl-3-pentylazetidin-1-yl)-3-(4-methoxyphenyl)propan-1-one are obtained with a yield of 86%.

Workup

  1. customthe solvents are evaporated off
  2. washwashed with 1N sodium hydroxide
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fb3970cb3d97423e9e3e5d301f2c097c
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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