Lithium Hydroxide → HCID 22632528, compound

HRID 2417541Notes

Reaction equation

HRID 2417541 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26](OC)=O)[CH:21]=3)[C:10](=[O:30])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Li+].[Cl:35]C(OCC)=O.[BH4-].[Na+].CS(Cl)(=O)=O>C1COCC1.ClCCl.C(OCC)(=O)C.C(N(CC)CC)C>[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][Cl:35])[CH:21]=3)[C:10](=[O:30])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

10

Reactant 5

HCID 3939Lithium HydroxideHCID 10928Ethyl chloroformateHCID 31297Methanesulfonyl chlorideHCID 4311764Sodium borohydrideHCID 22632602HCID 22632602, compound

Product 1

HCID 22632528HCID 22632528, compound

Reagents, catalysts & solvents 4

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

145 mg (0.32 mmol) of 4-(4-chlorobenzoyl)-1-(3-methoxycarbonylbenzyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on obtained in step 1 was dissolved in 3 ml of THF. 1.6 ml of 1 M aqueous lithium hydroxide solution was added to the obtained solution, and they were stirred overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 5 ml of THF. 0.1 ml (0.7 mmol) of triethylamine and 0.05 ml (0.5 mmol) of ethyl chloroformate were added to the obtained solution under cooling with ice, and they were stirred for 30 minutes. A piece of ice and 50 mg (1.4 mmol) of sodium borohydride were added to the obtained mixture. The temperature was elevated to room temperature, and the obtained mixture was stirred overnight. The solvent was evaporated, and the obtained crude product was dissolved in 8 ml of dichloromethane. 0.03 ml (0.22 mmol)) of triethylamine and 0.01 ml (0.13 mmol) of methanesulfonyl chloride were added to the obtained solution under cooling with ice, and they were stirred overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the crude product was obtained. After the purification by the silica gel column chromatography, the title compound was obtained.

Workup

  1. temperatureunder cooling with ice, and they
  2. stirringwere stirred for 30 minutes
  3. customwas elevated to room temperature
  4. stirringthe obtained mixture was stirred overnight
  5. customThe solvent was evaporated
  6. customthe obtained crude product
  7. temperatureunder cooling with ice, and they
  8. stirringwere stirred overnight
  9. customAfter the purification by the silica gel column chromatography

Sources & evidence

ORD record
ord-0c956b5e9c684f29aa812978f6ea970d
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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