Acetic Acid → Diethyl [2-(4-(4-chlorobenzoyl)-2-oxo-1-(4-(1-pyrrolidinecarbonyl)benzyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]-diazepin-8-yl)ethyl]phosphonate

HRID 2417489노트

반응식

HRID 2417489 반응식
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([N:8]([CH2:27][C:28](OCC)=[O:29])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][C:11]=2[NH2:26])=[O:7])=[CH:4][CH:3]=1.[N:35]1([C:40]([C:42]2[CH:49]=[CH:48][C:45]([CH:46]=O)=[CH:44][CH:43]=2)=[O:41])[CH2:39][CH2:38][CH2:37][CH2:36]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C>ClCCl.[OH-].[Na+].C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:9][C:10]3[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][P:18](=[O:19])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[CH:12][C:11]=3[N:26]([CH2:46][C:45]3[CH:44]=[CH:43][C:42]([C:40]([N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)=[O:41])=[CH:49][CH:48]=3)[C:28](=[O:29])[CH2:27]2)=[O:7])=[CH:33][CH:34]=1

참가 물질

10

반응물 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 127880444-(Pyrrolidine-1-carbonyl)benzaldehydeHCID 86589876HCID 86589876, 화합물

생성물 1

HCID 60123509Diethyl [2-(4-(4-chlorobenzoyl)-2-oxo-1-(4-(1-pyrrolidinecarbonyl)benzyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]-diazepin-8-yl)ethyl]phosphonate

시약·촉매·용매 4

HCID 702Ethanol용매HCID 6344Dichloromethane용매3회HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

실험 절차

240 mg (0.47 mmol) of ethyl ((4-chlorobenzoyl)-(4-(2-(diethoxyphosphoryl)ethyl)-2-aminobenzyl)amino)acetate and 105 mg (0.52 mmol) of 4-(1-pyrrolidinecarbonyl)benzaldehyde were dissolved in 10 ml of dichloromethane. 0.054 ml (0.94 mmol) of acetic acid was added to the obtained solution. They were stirred at room temperature for 30 minutes. 248 mg (1.18 mmol) of sodium triacetoxyborohydride was added to the obtained mixture and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in a mixture of 4 ml of 1 N sodium hydroxide and 2 ml of ethanol, and the solution was stirred at room temperature for 5 hours. After the treatment with ethyl acetate by an ordinary method, the obtained crude product was dissolved in 10 ml of dichloromethane. 95 mg (0.56 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.14 ml (0.94 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. The solvent was evaporated and the obtained crude product was treated in the same manner as in step 3 in Example 1 to obtain the title compound.

후처리

  1. stirringwere stirred at room temperature overnight
  2. stirringthe solution was stirred at room temperature for 5 hours
  3. stirringwere stirred overnight
  4. customThe solvent was evaporated
  5. customthe obtained crude product
  6. additionwas treated in the same manner as in step 3 in Example 1

출처 및 근거

ORD 기록
ord-27f52530310940de99e9f26385f32395
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06825191B2

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