Methanol → HCID 18612750, compound

HRID 1264600Notes

Reaction equation

HRID 1264600 reaction equation
[CH3:1][O:2][CH2:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][N:9]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:8]([C:28]([O:30][CH3:31])=[O:29])[CH2:7]1)=O.B.CO>O1CCCC1>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([S:17]([N:9]2[CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:6]([CH2:4][CH2:3][O:2][CH3:1])[CH2:7][CH:8]2[C:28]([O:30][CH3:31])=[O:29])(=[O:18])=[O:19])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 18612859HCID 18612859, compound

Product 1

HCID 18612750HCID 18612750, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.6 g (3.57 mmol) of methyl 1-(methoxyacetyl)-4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate and 32 ml of borane in tetrahydrofuran (1.0 M) was refluxed under nitrogen overnight. Methanol was added and the solvent removed. To the residue was added 25 ml of CH2Cl2 and 25 ml of 2 N HCl and the mixture stirred at room temperature for 1 hour. The organic layer was separated and washed with H2O and concentrated to dryness. The residue was triturated with ethyl acetate-hexane, cooled and filtered to give 1.2 g of white crystals, m.p. 86°-90° C.; Mass spectrum (ES) 435.4 (M+H). Anal. for C21H26N2O6S: Calc'd: C, 58.1; H, 6.0; N, 6.5; Found: C, 58.5; H, 6.0; N, 6.5.

Workup

  1. temperaturewas refluxed under nitrogen overnight
  2. customthe solvent removed
  3. additionTo the residue was added 25 ml of CH2Cl2 and 25 ml of 2 N HCl
  4. customThe organic layer was separated
  5. washwashed with H2O
  6. concentrationconcentrated to dryness
  7. customThe residue was triturated with ethyl acetate-hexane
  8. temperaturecooled
  9. filtrationfiltered

Sources & evidence

ORD record
ord-bc47b593ff58444a9105f09b8eae9c77
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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