Ammonium Bicarbonate → HCID 15871740, compound

HRID 1738908Notes

Reaction equation

HRID 1738908 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]([CH3:19])([CH3:18])[CH2:14][N:15]([CH3:17])[CH3:16])[C:10](=[O:20])[C@@H:9]([CH2:21][C:22](O)=[O:23])[O:8][C@H:7]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[C:6]=2[CH:35]=1.C(N1C=CN=C1)([N:38]1C=CN=C1)=O.C(=O)(O)[O-].[NH4+]>CN(C)C=O.C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]([CH3:19])([CH3:18])[CH2:14][N:15]([CH3:17])[CH3:16])[C:10](=[O:20])[C@@H:9]([CH2:21][C:22]([NH2:38])=[O:23])[O:8][C@H:7]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[C:6]=2[CH:35]=1

Participants

6

Reactant 3

HCID 14013Ammonium BicarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 15871738HCID 15871738, compound

Product 1

HCID 15871740HCID 15871740, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

Trans-7-chloro-5-(1 -naphthyl)-1 -(2,2-dimethyl-3-dimethylamino-propyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid (1.16 g, 2.35 mmol) and 1,1'-carbonyldiimidazole (1.91 g, 11.8 mmol) were dissolved in dimethylformamide (75 ml). Stirring for 1 h at room temperature was followed by addition of ammonium bicarbonate (1.86 g, 23.5 mmol) in one portion to the reaction mixture, which was stirred for further 18 hours at room temperature. The solvent was concentrated under reduced pressure and the residue flash chromatographed directly (dichloromethane/methanol/aqueous ammonia 99:1:0.1 to 98:2:0.2). The solid was taken up in dichloromethane and a stoichiometric amount of 1N HCl in ether was added. Removal of the solvent provided a solid which was dissolved in ethanol and precipitated with ether to give the title compound (0.42 g, 36%) as a colorless solid.

Workup

  1. stirringwas stirred for further 18 hours at room temperature
  2. concentrationThe solvent was concentrated under reduced pressure
  3. customthe residue flash chromatographed directly (dichloromethane/methanol/aqueous ammonia 99:1:0.1 to 98:2:0.2)
  4. additiona stoichiometric amount of 1N HCl in ether was added
  5. customRemoval of the solvent
  6. customprovided a solid which
  7. customprecipitated with ether

Sources & evidence

ORD record
ord-74434f672453482ba213cadb4ef99349
Source dataset
uspto-grants-1999_10
Patent number
US05965553

Reaction notes

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