Triethylamine → HCID 22632361, compound

HRID 2417493Notes

Reaction equation

HRID 2417493 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][C:17]([C:19](O)=[O:20])=[CH:18][C:12]=3[N:11]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[O:30])=[CH:25][CH:24]=3)[C:10](=[O:36])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.C(OCC)(=O)C>[OH:20][CH2:19][C:17]1[CH:16]=[CH:15][C:13]2[CH2:14][N:8]([C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:38][CH:37]=3)[CH2:9][C:10](=[O:36])[N:11]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([N:31]4[CH2:35][CH:34]=[CH:33][CH2:32]4)=[O:30])=[CH:25][CH:24]=3)[C:12]=2[CH:18]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 22632665HCID 22632665, compound

Product 1

HCID 22632361HCID 22632361, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

650 mg (1.22 mmol) of 4-(4-chlorobenzoyl)-2-oxo-1-[4-(1-pyrrolidinecarbonyl)benzyl]-2,3,4,5-tetrahydro-1H-benzo[e][1,4]-diazepine-8-carboxylic acid was dissolved in 50 ml of THF. 0.42 ml (2.4 mmol) of triethylamine and 0.15 ml (0.63 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 was added to the obtained mixture, and then 92 mg (1.1 mmol) of sodium borohydride was added thereto. The temperature was elevated to room temperature, and the obtained mixture was stirred overnight. After the treatment with ethyl acetate as the extracting solvent, the title compound was obtained.

Workup

  1. temperatureunder cooling with ice, and they
  2. additionA piece of ice was added to the obtained mixture
  3. customwas elevated to room temperature
  4. stirringthe obtained mixture was stirred overnight

Sources & evidence

ORD record
ord-c8a249b27299459aa9c640db50fb345d
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

Loading…