4-Methylmorpholine → (r)-2-[n-(4-Chlorophenyl)carbamoyloxy]-n-[4-(2-methoxyiminopiperidin-1-yl)phenyl]-2-phenylacetamide

HRID 350674Notes

Reaction equation

HRID 350674 reaction equation
CN1CCOCC1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([O:18][C@H:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]([OH:22])=O)=[O:17])=[CH:11][CH:10]=1.[CH3:29][O:30][N:31]=[C:32]1[CH2:37][CH2:36][CH2:35][CH2:34][N:33]1[C:38]1[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=1.Cl.CN(C)CCCN=C=NCC.O.OC1C2N=NNC=2C=CC=1.C(=O)([O-])O.[Na+]>CN(C=O)C>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]([O:18][C@H:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]([NH:44][C:41]2[CH:42]=[CH:43][C:38]([N:33]3[CH2:34][CH2:35][CH2:36][CH2:37][C:32]3=[N:31][O:30][CH3:29])=[CH:39][CH:40]=2)=[O:22])=[O:17])=[CH:13][CH:14]=1

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12992874(R)-(4-chlorophenylcarbamoyloxy)phenylacetic acidHCID 854347211-(4-aminophenyl)-piperidin-2-one O-methyl oximeHCID 178526939HCID 178526939, compound

Product 1

HCID 91483835(r)-2-[n-(4-Chlorophenyl)carbamoyloxy]-n-[4-(2-methoxyiminopiperidin-1-yl)phenyl]-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.2 101 mg (1.00 mmol) of 4-methylmorpholine are added to a solution of 183 mg (0.600 mmol) of (R)-(4-chlorophenylcarbamoyloxy)phenylacetic acid, 129 mg (0.588 mmol) of 1-(4-aminophenyl)piperidin-2-one O-methyl oxime, 192 mg (1.00 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) and 91.9 mg (0.600 mmol) of hydroxybenzotriazole hydrate (HOBt) in 1 ml of DMF, and the mixture is stirred at room temperature for 24 hours. The reaction mixture is introduced into saturated sodium hydrogencarbonate solution, and the resultant precipitate is filtered off. The precipitate is chromatographed on a silica-gel column with petroleum ether/ethyl acetate as eluent, giving (R)-2-[N-(4-chlorophenyl)carbamoyloxy]-N-[4-(2-methoxyiminopiperidin-1-yl)phenyl]-2-phenylacetamide (“AA”) as a colourless solid; ESI 507.

Workup

  1. filtrationthe resultant precipitate is filtered off
  2. customThe precipitate is chromatographed on a silica-gel column with petroleum ether/ethyl acetate as eluent

Sources & evidence

ORD record
ord-4131f17bca1b4857b1fe69bb65f23642
Source dataset
uspto-grants-2007_02
Patent number
US07183277B2

Reaction notes

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