Diisopropylethylamine → Ethyl 2-hydroxy-4-phenyl-3-(2-(2-phenylthiazol-4-yl)nicotinamido)butanoate

HRID 1400231노트

반응식

HRID 1400231 반응식
Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[C:33]1([C:39]2[S:40][CH:41]=[C:42]([C:44]3[N:52]=[CH:51][CH:50]=[CH:49][C:45]=3[C:46]([OH:48])=O)[N:43]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[Cl-].[CH2:54]([O:56][C:57](=[O:69])[CH:58]([OH:68])[CH:59]([NH3+:67])[CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[CH3:55]>ClCCl>[OH:68][CH:58]([CH:59]([NH:67][C:46](=[O:48])[C:45]1[CH:49]=[CH:50][CH:51]=[N:52][C:44]=1[C:42]1[N:43]=[C:39]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[S:40][CH:41]=1)[CH2:60][C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)[C:57]([O:56][CH2:54][CH3:55])=[O:69]

참가 물질

7

반응물 5

HCID 81531Diisopropylethylamine2회HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67540106(2-Phenylthiazol-4-yl)nicotinic acidHCID 86644788HCID 86644788, 화합물

생성물 1

HCID 67540490Ethyl 2-hydroxy-4-phenyl-3-(2-(2-phenylthiazol-4-yl)nicotinamido)butanoate수율 94.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
5 °C

실험 절차

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC) (700 mg, 3.65 mmol), 1-hydroxybenzotriazole hydrate (550 mg, 3.59 mmol) and N,N-diisopropylethylamine (DIPEA) (1.2 ml, 6.87 mmol) were successively added to a solution of (2-phenylthiazol-4-yl)nicotinic acid (820 mg, 2.90 mmol) and 4-ethoxy-3-hydroxy-4-oxo-1-phenylbutan-2-aminium chloride (800 mg, 3.08 mmol) in dichloromethane (70 ml) at 5° C., and the mixture stirred at 5° C. for about 5 minutes. A pH of 8 was adjusted by adding 0.6 ml of DIPEA, the mixture stirred for 1 hour at 5° C. and then overnight at room temperature. The mixture then was concentrated under reduced pressure, poured into 200 ml of water, the precipitate formed was filtered off with suction and dried in vacuo to give 1.33 g of the title product as white amorphous solid.

후처리

  1. stirringthe mixture stirred for 1 hour at 5° C.
  2. customovernight
  3. customat room temperature
  4. concentrationThe mixture then was concentrated under reduced pressure
  5. additionpoured into 200 ml of water
  6. customthe precipitate formed
  7. filtrationwas filtered off with suction
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-8804e32a46d445349b926fe02932887b
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906941B2

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