Ethyl Acetate → HCID 10415114, compound

HRID 1816449Notes

Reaction equation

HRID 1816449 reaction equation
C(O[CH:4](SCC)[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:43])[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[C:39]([O:40][CH3:41])=[CH:38][C:28]3[C:29](=[O:37])[N:30]4[CH2:36][CH2:35][CH2:34][C@H:31]4[CH2:32][NH:33][C:27]=3[CH:26]=2)=[CH:13][C:12]=1[NH2:42])C.C([O-])([O-])=O.[Ca+2].CCOC(C)=O>CC#N.O.Cl[Hg]Cl>[CH3:18][O:17][C:15]1[C:14]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[C:39]([O:40][CH3:41])=[CH:38][C:28]3[C:29](=[O:37])[N:30]4[CH2:36][CH2:35][CH2:34][C@H:31]4[CH2:32][NH:33][C:27]=3[CH:26]=2)=[CH:13][C:12]2[N:42]=[CH:4][C@@H:5]3[CH2:9][CH2:8][CH2:7][N:6]3[C:10](=[O:43])[C:11]=2[CH:16]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 10112Calcium CarbonateHCID 86594407HCID 86594407, compound2×

Product 1

HCID 10415114HCID 10415114, compound

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A solution of the (2S)-N-{4-[4-(7-Methoxy-(11aS)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one-8-yloxy)butoxy]-5-methoxy-2-aminobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal of formula IV. (672 mg, 1 mmol), HgCl2 (794 mg, 2.93 mmol) and CaCO3 (300 mg, 3 mmol) in CH3CN/H2O (4:1, 15 mL) was stirred at room temperature for 12 h until TLC (EtOAc), indicates complete loss of starting material. Then organic layer is evaporated in vacuum and the residue is diluted with EtOAc. To this saturated NaHCO3 was added slowly at room temperature and the mixture is filtered through celite and washed with ethylacetate. The filterate is evaporated in vacuum to get crude 7-Methoxy-8-{4-[7-methoxy-(11aS)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one-8-yloxy]butoxy}-(11aS)-1,2,3,11a-tetrahy-dro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one of formula V, which was further purified by column chromatography on silica gel eluting with methanol:EtOAc (2:8).

Workup

  1. customThen organic layer is evaporated in vacuum
  2. additionthe residue is diluted with EtOAc
  3. additionTo this saturated NaHCO3 was added slowly at room temperature
  4. filtrationthe mixture is filtered through celite
  5. washwashed with ethylacetate
  6. customThe filterate is evaporated in vacuum

Sources & evidence

ORD record
ord-0258f7abaad8466896a9209e33d0557d
Source dataset
uspto-grants-2005_04
Patent number
US06884799B2

Reaction notes

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