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

HRID 1400231ノート

反応式

HRID 1400231 の反応式
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]

参加物

7

反応物 5

HCID 81531Diisopropylethylamine2 回HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67540106(2-Phenylthiazol-4-yl)nicotinic acidHCID 86644788HCID 86644788、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8804e32a46d445349b926fe02932887b
出典データセット
uspto-grants-2014_12
特許番号
US08906941B2

反応ノート

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