Methanol → HCID 86594407, compound

HRID 1816448Notes

Reaction equation

HRID 1816448 reaction equation
[CH2:1]([O:3][CH:4]([S:46][CH2:47][CH3:48])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:45])[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[N+:42]([O-])=O)[CH3:2].CO.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([O:3][CH:4]([S:46][CH2:47][CH3:48])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:45])[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])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 86594408HCID 86594408, compound2×

Product 1

HCID 86594407HCID 86594407, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal (702 mg, 1.0 mmol) of the formula III was dissolved in dichloromethane (5 mL), methanol (10 mL) and added SnCl2.2H2O (1.124 g, 5.0 mmol) was refluxed for 1.5 h. The reaction mixture was then carefully adjusted to pH 8 with saturated NaHCO3 solution and then extracted with ethylacetate (3×20 mL). The combined organic phase was dried over Na2SO4 and evaporated under vacuum to afford the crude (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 IV.

Workup

  1. temperaturewas refluxed for 1.5 h
  2. extractionextracted with ethylacetate (3×20 mL)
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-7968b5f0c9f14891804bc3df4aab86d8
Source dataset
uspto-grants-2005_04
Patent number
US06884799B2

Reaction notes

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