Dichloromethane → HCID 20506149, compound

HRID 354760Notes

Reaction equation

HRID 354760 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([CH3:15])([CH3:14])[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:6]=2[CH:23]=1.Cl.[NH2:25][C:26]([CH3:31])([CH3:30])[C:27](Cl)=[O:28].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>O1CCCC1.O>[NH2:25][C:26]([CH3:31])([CH3:30])[C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([CH3:15])([CH3:14])[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:6]=2[CH:23]=1)=[O:28]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 205061627-amino-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-oneHCID 214155052-Amino-2-methylpropanoyl chloride hydrochloride

Product 1

HCID 20506149HCID 20506149, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

8 g (0.026 mol) of 7-amino-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one are stirred at room temperature for 1 hour with 5 g of α-aminoisobutyric acid chloride hydrochloride in 30 ml of tetrahydrofuran, 8 g of potassium carbonate are subsequently added thereto and, after a further 15 minutes, the mixture is treated with methylene chloride and water. The organic phase is separated and the aqueous phase is extracted four times with methylene chloride. The combined organic extracts are dried and evaporated. The residue is purified on 350 g of silica gel with methylene chloride/ethyl acetate (1:1) and ethyl acetate as the elution agent. From ethyl acetate/ether there is obtained 2-amino-N-[5-(o-fluorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-2-methylpropionamide of melting point 250°.

Workup

  1. additionare subsequently added
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted four times with methylene chloride
  4. customThe combined organic extracts are dried
  5. customevaporated
  6. customThe residue is purified on 350 g of silica gel with methylene chloride/ethyl acetate (1:1) and ethyl acetate as the elution agent

Sources & evidence

ORD record
ord-11951ee022d94d62a7ce787340d00e77
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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