Ammonium Chloride → HCID 21701441, compound

HRID 1596362Notes

Reaction equation

HRID 1596362 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:16]2[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:15]=2[N:14]([CH2:30][C:31](N(C)C2C=CC=CN=2)=[O:32])[C:13]1=[O:41])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:42]1([Mg]Cl)[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[C:16]2[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:15]=2[N:14]([CH2:30][C:31]([CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[O:32])[C:13]1=[O:41])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 21701405HCID 21701405, compoundHCID 178478990HCID 178478990, compound

Product 1

HCID 21701441HCID 21701441, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (3RS)-3-benzyloxycarbonylamino-5-cyclohexyl-2,3-dihydro-9-methyl-1-[N-methyl-N-(2-pyridyl)amino]carbonylmethyl-1H-1,4-benzodiazepin-2-one (400 mg) in tetrahydrofuran (4 ml) was added cyclohexyl magnesium chloride (1.08 ml) under stirring, at 0° C. The mixture was stirred for twenty minutes under the same conditions and at room temperature overnight. Ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture. The separated organic layer was washed with 0.1N aqueous hydrochloric acid, water, a saturated aqueous sodium bicarbonate solution and brine successively and dried under magnesium sulfate. The solvent was removed in vacuo to afford a residue, which was subjected to column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (20:1) to give (3RS)-3-benzyloxycarbonylamino-5-cyclohexyl-1-cyclohexylcarbonylmethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one.

Workup

  1. stirringThe mixture was stirred for twenty minutes under the same conditions and at room temperature overnight
  2. washThe separated organic layer was washed with 0.1N aqueous hydrochloric acid, water
  3. dry with materiala saturated aqueous sodium bicarbonate solution and brine successively and dried under magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customto afford a residue, which

Sources & evidence

ORD record
ord-def6c96c1d7546d1b6b7a3ac28adfe8f
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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