Methanol → HCID 86594410, compound

HRID 1816457Notes

Reaction equation

HRID 1816457 reaction equation
[CH2:1]([O:3][CH:4]([S:47][CH2:48][CH3:49])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:46])[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[C:40]([O:41][CH3:42])=[CH:39][C:29]3[C:30](=[O:38])[N:31]4[CH2:37][CH2:36][CH2:35][C@H:32]4[CH2:33][NH:34][C:28]=3[CH:27]=2)=[CH:13][C:12]=1[N+:43]([O-])=O)[CH3:2].CO.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([O:3][CH:4]([S:47][CH2:48][CH3:49])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:46])[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[C:40]([O:41][CH3:42])=[CH:39][C:29]3[C:30](=[O:38])[N:31]4[CH2:37][CH2:36][CH2:35][C@H:32]4[CH2:33][NH:34][C:28]=3[CH:27]=2)=[CH:13][C:12]=1[NH2:43])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 86594409HCID 86594409, compound

Product 1

HCID 86594410HCID 86594410, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The (4R)-hydroxy-(2S)-N-{4-[5-(7-Methoxy-(11aS)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one-8-yloxy)pentyloxy]-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal III (732 mg, 1.0 mmol) 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 ethyl acetate (3×20 mL). The combined organic phase was dried over Na2SO4 and evaporated under vacuum to afford the crude (4R)-hydroxy-(2S)-N-{4-[5-(7-Methoxy-(11aS)-1,2,3,10,11,11la-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5-one-8-yloxy)pentyloxy]-5-methoxy-2-aminobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal of formula IV.

Workup

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

Sources & evidence

ORD record
ord-b2ef2ca719e34d51bc374aed4c3dcc8d
Source dataset
uspto-grants-2005_04
Patent number
US06884799B2

Reaction notes

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