Ethanolamine → HCID 68973505, 화합물

HRID 727262노트

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HRID 727262 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C@H:10]([CH2:24][C:25]([OH:27])=O)[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[CH2:42]([CH2:44][NH2:45])[OH:43]>O1CCCC1.O.CN(C)C=O>[OH:43][CH2:42][CH2:44][NH:45][C:25](=[O:27])[CH2:24][C@@H:10]1[N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:14]2[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]12

참가 물질

8

반응물 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 668281072-((9S)-7-(4-chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo(8.3.0.0,2,6)trideca-2(6),4,7,10,12-pentaen-9-yl)acetic acid

생성물 1

HCID 68973505HCID 68973505, 화합물수율 29.5%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매2회

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온도
-5 °C

실험 절차

(S)-4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid (7.0 g) and triethylamine (2.73 ml) are added to a mixed solvent of dimethylformamide (70 ml) and tetrahydrofuran (30 ml). The mixture is cooled to -5° C., and pivaloyl chloride (2.38 ml) is dropwise added at said temperature. Ten minutes later, a solution of ethanolamine (1.17 g) in tetrahydrofuran (10 ml) is dropwise added at said temperature, and the mixture is stirred at room temperature for 2 hours. Water is added to the reaction mixture, and the mixture is extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The solvent is distilled away, and the residue is purified by column chromatography (chloroform: methanol =50: 1) and recrystallized from ethyl acetate to give 2.29 g of (S)-N-(2-hydroxyethyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide 1/4 hydrate, melting point 254°-255° C.

후처리

  1. extractionthe mixture is extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent is distilled away
  5. customthe residue is purified by column chromatography (chloroform: methanol =50: 1)
  6. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-58e0de326b254e8f9ed58e5d6aa2dedb
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05712274

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