Ammonia → 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 methylamide

HRID 80976Notes

Reaction equation

HRID 80976 reaction equation
CN.[C:3]([O-:6])([O-])=O.[K+].[K+].ClC(OC1C=C[C:16]([N+:19]([O-])=O)=CC=1)=O.[OH:22][C:23]([CH3:53])([CH3:52])[CH2:24][C@@:25]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[O:30][C:29](=[O:31])[N:28]([C@H:32]([C:34]2[CH:39]=[CH:38][C:37]([CH:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)=[CH:36][CH:35]=2)[CH3:33])[CH2:27][CH2:26]1.N>C(#N)C.CCN(CC)CC>[CH3:16][NH:19][C:3]([N:43]1[CH2:44][CH2:45][CH:40]([C:37]2[CH:38]=[CH:39][C:34]([C@@H:32]([N:28]3[CH2:27][CH2:26][C@:25]([CH2:24][C:23]([OH:22])([CH3:52])[CH3:53])([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[O:30][C:29]3=[O:31])[CH3:33])=[CH:35][CH:36]=2)[CH2:41][CH2:42]1)=[O:6]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 6329MethylamineHCID 11430Potassium CarbonateHCID 821294-Nitrophenyl chloroformateHCID 58109308(S)-6-(2-Hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-piperidin-4-yl-phenyl)-ethyl]-[1,3]oxazinan-2-one

Product 1

HCID 451014124-(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 methylamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

MeNH2*HCl (27 mg) and K2CO3 (93 mg) were added to a solution of 4-nitrophenyl chloroformate (66 mg) in acetonitrile (2 mL) at room temperature. The resulting mixture was stirred at room temperature for 4 h, before (S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-piperidin-4-yl-phenyl)-ethyl]-[1,3]oxazinan-2-one (110 mg) and NEt3 (53 μL) were added. The mixture was further stirred at room temperature overnight. Then, diluted aqueous ammonia solution was added and the resulting mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was purified by HPLC on reversed phase (MeOH/H2O/NH3) to afford the title compound.

Workup

  1. additionwere added
  2. filtrationthe resulting mixture was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by HPLC on reversed phase (MeOH/H2O/NH3)

Sources & evidence

ORD record
ord-52e9d8b331424c9fa1019b5ac0920e80
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Reaction notes

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