Triethylamine → N-[4-[4-(2,4-Diamino-6-propyl-5-pyrimidinyl)-1-piperazinyl]benzoyl]-L-glutamic acid, diethyl ester

HRID 371468

반응식

HRID 371468 반응식
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[C:4]([CH2:24][CH2:25][CH3:26])[N:3]=1.P(C#N)(=O)(OCC)OCC.C(N(CC)CC)C.Cl.[NH2:45][C@H:46]([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH2:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50]>CN(C)C=O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH:45][C@H:46]([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH2:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])=[O:20])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[C:4]([CH2:24][CH2:25][CH3:26])[N:3]=1

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 73960Glutamic acid diethyl ester hydrochlorideHCID 76257Diethyl cyanophosphonateHCID 134783504-[4-(2,4-Diamino-6-propyl-5-pyrimidinyl]-1-piperazinyl]benzoic acid

생성물 1

HCID 13478344N-[4-[4-(2,4-Diamino-6-propyl-5-pyrimidinyl)-1-piperazinyl]benzoyl]-L-glutamic acid, diethyl ester수율 38.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A mixture of 3.2 g (0.0091 mole) of 4-[4-(2,4-diamino-6-propyl-5-pyrimidinyl]-1-piperazinyl]benzoic acid, 4.9 g (0.030 mole) of diethyl phosphorocyanidate and 4.2 ml (0.030 mole) of triethylamine in 200 ml of of N,N-dimethylformamide (dried over 4 Å molecular sieves overnight) was stirred at room temperature for two hours. To the resulting clear solution was added a mixture of 2.4 g (0.010 mole) of diethyl glutamate hydrochloride and 1.4 ml (0.010 mole) of triethylamine in 10 ml of N,N-dimethylformamide, and the solution was stirred for another hour. The solvent was removed under high vacuum (0.1 mm, dry ice-2-propanol trap) at 40° C. The gummy residue was poured into 100 ml of ice water. The solid was collected and recrystallized from N,N-dimethylformamide to give 1.9 g of the product as an off-white powder; mp 175°-180° C.

후처리

  1. additionTo the resulting clear solution was added
  2. stirringthe solution was stirred for another hour
  3. customThe solvent was removed under high vacuum (0.1 mm, dry ice-2-propanol trap) at 40° C
  4. additionThe gummy residue was poured into 100 ml of ice water
  5. customThe solid was collected
  6. customrecrystallized from N,N-dimethylformamide

출처 및 근거

ORD 기록
ord-cfeba9dfe18b4c19a834bff7925160de
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04532240

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