Sodium Hydroxide → HCID 11952999, compound

HRID 1241465Notes

Reaction equation

HRID 1241465 reaction equation
[C:1]([O:5][C:6](=[O:44])[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]([O:24]C)=[O:23])=[CH:21][C:16]=2[C:15](=[O:26])[N:14]([C@@H:27]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[CH3:28])[C@@H:13]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=2)[C:12]1=[O:43])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO.O>[C:1]([O:5][C:6]([CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]([OH:24])=[O:23])=[CH:21][C:16]=2[C:15](=[O:26])[N:14]([C@@H:27]([C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)[CH3:28])[C@@H:13]([C:36]2[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=2)[C:12]1=[O:43])=[O:44])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11952998HCID 11952998, compound

Product 1

HCID 11952999HCID 11952999, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 5-[(3S)-3-(4-chlorophenyl)-4-[(R)-1-(4-chlorophenyl)ethyl]-7-methoxycarbonyl-2,5-dioxo-3,4-dihydro-1H-1,4-benzodiazepin-1-yl]valeric acid tert-butyl ester (Example 32) (200 mg, 0.31 mmol) and NaOH (1N in water, 380 μL) in THF/MeOH/H2O (2 mL/400 μL/100 μL) was stirred at room temperature for 12 h. The mixture was evaporated to dryness. Then, the residue was dissolved in water (10 mL) and the pH was adjusted to 4 with 1N HCl. The solution was extracted with ether (3×20 mL), then the organic layer was dried (Na2SO4) and concentrated to dryness under reduced pressure. Filtration over silica gel afforded the title compound (150 mg, 77%): Mass spectrum (LCMS, ESI pos.): Calcd for C33H34Cl2IN2O6: 624.18; found 568.9 (M+H—t-bu).

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionThen, the residue was dissolved in water (10 mL)
  3. extractionThe solution was extracted with ether (3×20 mL)
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. concentrationconcentrated to dryness under reduced pressure
  6. filtrationFiltration over silica gel

Sources & evidence

ORD record
ord-2b030606f07742878007953928c26906
Source dataset
uspto-grants-2006_10
Patent number
US07115598B2

Reaction notes

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