Sodium Hydroxide → (R)-7-cyano-2,3,4,5-tetrahydro-4-(phenylacetyl)-3-(phenylmethyl)-1H-1,4-benzodiazepine

HRID 849417Notes

Reaction equation

HRID 849417 reaction equation
Cl.Cl.Cl.N1C=C(C[N:10]2[C:16]3[CH:17]=CC(C4C=NC=CC=4)=[CH:20][C:15]=3[CH2:14][N:13]([C:27](=[O:32])[C:28](F)(F)F)[CH:12]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:11]2)N=C1.CS(Cl)(=O)=O.[OH-].[Na+]>C(Cl)Cl>[C:11]([C:12]1[CH:33]=[CH:17][C:16]2[NH:10][CH2:11][C@@H:12]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:13]([C:27](=[O:32])[CH2:28][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:14][C:15]=2[CH:20]=1)#[N:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 178478619HCID 178478619, compound

Product 1

HCID 53636257(R)-7-cyano-2,3,4,5-tetrahydro-4-(phenylacetyl)-3-(phenylmethyl)-1H-1,4-benzodiazepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound B (28.5 mmol, 9.0 g) in CH2Cl2 (200 mL) was added TEA (142.5 mmol, 20 mL) and methanesulfonyl chloride (37.5 mmol, 2.9 mL). The mixture was stirred at rt for 1 hr, poured over 2N NaOH (500 mL) and extracted with 10%IPA-CH2Cl2 (3×250 mL). The combined organic layers were dried over Na2SO4, concentrated, and azeotroped with toluene to afford Compound C.

Workup

  1. extractionextracted with 10%IPA-CH2Cl2 (3×250 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customazeotroped with toluene

Sources & evidence

ORD record
ord-1b67a80e4a764b7c85c53e3fb82fd7f6
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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