Trifluoroacetic acid → (S)-6-(2-Hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-piperidin-4-yl-phenyl)-ethyl]-[1,3]oxazinan-2-one

HRID 2037812Notes

Reaction equation

HRID 2037812 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:26]=[CH:25][C:24]([C@@H:27]([N:29]3[CH2:34][CH2:33][C@:32]([CH2:41][C:42]([OH:45])([CH3:44])[CH3:43])([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[O:31][C:30]3=[O:46])[CH3:28])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.C([O-])(O)=O.[Na+]>ClCCl>[OH:45][C:42]([CH3:43])([CH3:44])[CH2:41][C@@:32]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:31][C:30](=[O:46])[N:29]([C@H:27]([C:24]2[CH:25]=[CH:26][C:21]([CH:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)=[CH:22][CH:23]=2)[CH3:28])[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 581097014-(4-{(S)-1-[(S)-6-(2-Hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58109308(S)-6-(2-Hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-piperidin-4-yl-phenyl)-ethyl]-[1,3]oxazinan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (0.40 mL) was added to a solution of 4-(4-{(S)-1-[(S)-6-(2-hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.29 g) in dichloromethane (10 mL). The resulting solution was stirred at room temperature overnight. Then, more dichloromethane was added and the solution was neutralized using aqueous saturated NaHCO3 solution. The organic phase was separated, washed with water, and dried (MgSO4). The solvent was removed under reduced pressure to give the title compound.

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2f1ff233742d460eb8f276a014cbeb4b
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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