Sodium Hydroxide → HCID 86671777, compound

HRID 513162Notes

Reaction equation

HRID 513162 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=3[NH:12][C:11](=[S:21])[C@H:10]([CH2:22][C:23]([O:25]C)=[O:24])[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=3[NH:12][C:11](=[S:21])[CH:10]([CH2:22][C:23]([OH:25])=[O:24])[N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 57465560Methyl [(3S)-5-(4-chlorophenyl)-7-(methyloxy)-2-thioxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]acetate

Product 1

HCID 86671777HCID 86671777, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of racemic Intermediate 6 (2.6 g, 6.7 mmol) in 1,4-dioxane (70 mL) at RT was added slowly 1N NaOH (13.5 mL) and the reaction mixture was stirred overnight before adding another 1N NaOH (13.5 mL). The mixture was then further stirred for 2 h before 1,4-dioxane was removed in vacuo. The aqueous layer was acidified with 1N HCl to ca pH 6 and extracted with DCM. The organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (1.9 g, 76% yield) as a yellow solid. LC/MS: m/z 375 [M(35Cl)+H]+, Rt=1.6 min.

Workup

  1. customwas removed in vacuo
  2. extractionextracted with DCM
  3. dry with materialThe organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02bd6ac5d0a64aaa96db3a5c823c7d35
Source dataset
uspto-grants-2015_08
Patent number
US09102677B2

Reaction notes

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