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 80968Notes

Reaction equation

HRID 80968 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 yield 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-ff0e0c3768f644dfa8e8ed001120b5ba
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Reaction notes

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