Ethyl Acetate → HCID 18714160, compound

HRID 279401Notes

Reaction equation

HRID 279401 reaction equation
[C:1]([O:4][C@H:5]1[CH2:14][N:13]2[C@H:7]([C:8](=[O:53])[NH:9][C:10]3[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]4[CH:31]=[C:30]([N+:32]([O-])=O)[C:29]([C:35]([N:37]5[CH2:41][CH2:40][CH2:39][C@H:38]5[CH:42](SCC)SCC)=[O:36])=[CH:28][C:27]=4[O:49][CH3:50])[C:17]([O:51][CH3:52])=[CH:16][C:11]=3[C:12]2=[O:15])[CH2:6]1)(=[O:3])[CH3:2].CCOC(C)=O>CC#N.O.Cl[Hg]Cl>[C:1]([O:4][C@H:5]1[CH2:14][N:13]2[C@H:7]([C:8](=[O:53])[NH:9][C:10]3[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]4[C:27]([O:49][CH3:50])=[CH:28][C:29]5[C:35](=[O:36])[N:37]6[CH2:41][CH2:40][CH2:39][C@@H:38]6[CH:42]=[N:32][C:30]=5[CH:31]=4)[C:17]([O:51][CH3:52])=[CH:16][C:11]=3[C:12]2=[O:15])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 18714162HCID 18714162, compound

Product 1

HCID 18714160HCID 18714160, compound

Reagents, catalysts & solvents 2

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

Procedure

A solution of the 8-(4-(4-(2-di(ethylsulfanyl)methyl-(2S)-tetrahydro-1H-1-pyrrolylcarbonyl)-2-methoxy-5-aminophenoxy)butoxy)-7-methoxy-5,11-dioxo-(2R,11aS)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-2-yl acetate of formula V (744 mg, 1 mmol), HgCl2 (794 mg, 2.93 mmol) and HgO (687 mg, 3.18 mmol) in CH3CN/H2O (3:1, 15 ml) was stirred at room temperature for 12 h until TLC (EtOAc) indicated complete loss of starting material. Then the organic layer was evaporated in a vacuum and the residue was diluted with EtOAc. To this, saturated NaHCO3 was added slowly at room temperature and the mixture was filtered through celite and washed with ethylacetate. The filtrate was evaporated in a vacuum to obtain crude 7-methoxy-8-(4-(7-methoxy-5-oxo-(11aR)-2,3,5,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-8-yloxy)butoxy)-5,11-dioxo-(2R,11aS)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-2-yl acetate of formula VI, which was further purified by column chromatography on silica gel by eluting first with ethylacetate to remove traces of mercuric salts and then with MeOH:CHCl3 (2:8).

Workup

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

Sources & evidence

ORD record
ord-1b4f3f6ac9c940558feec8e5ad960dfa
Source dataset
uspto-grants-2002_03
Patent number
US06362331B1

Reaction notes

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