Acetic Anhydride → HCID 45101409, compound

HRID 80969Notes

Reaction equation

HRID 80969 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[OH:15][C:16]([CH3:46])([CH3:45])[CH2:17][C@@:18]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:23][C:22](=[O:24])[N:21]([C@H:25]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[CH:29][CH:28]=2)[CH3:26])[CH2:20][CH2:19]1>CN(C)C1C=CN=CC=1.O1CCCC1.C(OCC)(=O)C>[C:8]([N:36]1[CH2:37][CH2:38][CH:33]([C:30]2[CH:31]=[CH:32][C:27]([C@@H:25]([N:21]3[CH2:20][CH2:19][C@:18]([CH2:17][C:16]([OH:15])([CH3:45])[CH3:46])([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[O:23][C:22]3=[O:24])[CH3:26])=[CH:28][CH:29]=2)[CH2:34][CH2:35]1)(=[O:10])[CH3:9]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 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 45101409HCID 45101409, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.10 mL), acetic anhydride (50 μL), and 4-dimethylaminopyridine (5 mg) were added consecutively to (S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-piperidin-4-yl-phenyl)-ethyl]-[1,3]oxazinan-2-one (0.12 g) dissolved in tetrahydrofuran (5 mL) at room temperature. The solution was stirred at room temperature for 4 h and then diluted with ethyl acetate. The resulting solution was washed with aqueous saturated NaHCO3 solution and brine and dried (Na2SO4). After removal of the solvent, the residue was purified by chromatography on silica gel (CH2Cl2/MeOH 98:2→90:10) to afford the title compound as a colorless foam-like solid.

Workup

  1. washThe resulting solution was washed with aqueous saturated NaHCO3 solution and brine
  2. dry with materialdried (Na2SO4)
  3. customAfter removal of the solvent
  4. customthe residue was purified by chromatography on silica gel (CH2Cl2/MeOH 98:2→90:10)

Sources & evidence

ORD record
ord-84d75490b6a54f05bbc748ecaffac42e
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Reaction notes

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