Methyl chloroformate → HCID 45101410, compound

HRID 80970Notes

Reaction equation

HRID 80970 reaction equation
C(N(CC)CC)C.Cl[C:9]([O:11][CH3:12])=[O:10].[OH:13][C:14]([CH3:44])([CH3:43])[CH2:15][C@@:16]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:21][C:20](=[O:22])[N:19]([C@H:23]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)=[CH:27][CH:26]=2)[CH3:24])[CH2:18][CH2:17]1>ClCCl>[CH3:12][O:11][C:9]([N:34]1[CH2:35][CH2:36][CH:31]([C:28]2[CH:27]=[CH:26][C:25]([C@@H:23]([N:19]3[CH2:18][CH2:17][C@:16]([CH2:15][C:14]([OH:13])([CH3:43])[CH3:44])([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[O:21][C:20]3=[O:22])[CH3:24])=[CH:30][CH:29]=2)[CH2:32][CH2:33]1)=[O:10]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 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 45101410HCID 45101410, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.10 mL) and methyl chloroformate (24 μL) 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 dichloromethane (5 mL) at room temperature. The resulting solution was stirred at room temperature overnight and then diluted with dichloromethane. The resulting solution was washed with water and brine and dried (Na2SO4). After removal of the solvent, the residue was purified by chromatography on silica gel (CH2Cl2/MeOH 99:1→90:10) to afford the title compound as a foam-like solid.

Workup

  1. washThe resulting solution was washed with water 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 99:1→90:10)

Sources & evidence

ORD record
ord-65afd247dabf40c0bf07b38d05555a76
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Reaction notes

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