Diisopropylethylamine → (E)-Hept-2-enoic acid [(S)-2-(3,5-difluorophenyl)-1-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraazatricyclo[17.3.0.07,11]docos-3-ylcarbamoyl)-ethyl]-amide

HRID 751767

反応式

HRID 751767 の反応式
FC(F)(F)C([O-])=O.[F:8][C:9]1[CH:10]=[C:11]([CH2:16][C@H:17]([NH3+:51])[C:18](=[O:50])[NH:19][C@H:20]2[CH2:41][O:40][C:39](=[O:42])[C@H:38]3[N:34]([CH2:35][CH2:36][CH2:37]3)[C:33](=[O:43])[C@H:32]([CH3:44])[NH:31][C:30](=[O:45])[C@H:29]([CH3:46])[N:28]([CH3:47])[C:27](=[O:48])[C@H:26]3[N:22]([CH2:23][CH2:24][CH2:25]3)[C:21]2=[O:49])[CH:12]=[C:13]([F:15])[CH:14]=1.[C:52](O)(=[O:59])/[CH:53]=[CH:54]/[CH2:55][CH2:56][CH2:57][CH3:58].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>ClCCl>[F:8][C:9]1[CH:10]=[C:11]([CH2:16][C@H:17]([NH:51][C:52](=[O:59])/[CH:53]=[CH:54]/[CH2:55][CH2:56][CH2:57][CH3:58])[C:18](=[O:50])[NH:19][C@H:20]2[CH2:41][O:40][C:39](=[O:42])[C@H:38]3[N:34]([CH2:35][CH2:36][CH2:37]3)[C:33](=[O:43])[C@H:32]([CH3:44])[NH:31][C:30](=[O:45])[C@H:29]([CH3:46])[N:28]([CH3:47])[C:27](=[O:48])[C@H:26]3[N:22]([CH2:23][CH2:24][CH2:25]3)[C:21]2=[O:49])[CH:12]=[C:13]([F:15])[CH:14]=1

参加物

6

反応物 4

HCID 81531Diisopropylethylamine2 回HCID 52827092-Heptenoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86598030(S)-2-(3,5-Difluorophenyl)-1-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraaza-tricyclo[17.3.0.07,11]docos-3-ylcarbamoyl)-ethylammonium 2,2,2-trifluoroacetate

生成物 1

HCID 11422732(E)-Hept-2-enoic acid [(S)-2-(3,5-difluorophenyl)-1-((3S,7S,13S,16S,19S)-13,16,17-trimethyl-2,6,12,15,18-pentaoxo-5-oxa-1,11,14,17-tetraazatricyclo[17.3.0.07,11]docos-3-ylcarbamoyl)-ethyl]-amide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

2.89 g (2.75 mmol) of the compound from example 13A and 458.8 mg (3.58 mmol) of trans-2-heptenoic acid are introduced into dichloromethane (20 ml), cooled to 0° C., then treated with 2.09 g (5.51 mmol) of HATU and 462.7 mg (3.58 mmol) of ethyldiisopropylamine. The solution is stirred at 0° C. for 30 min, then a further 925.3 mg (7.16 mmol) of ethyldiisopropylamine are added, and it is stirred at room temperature for 18 h. The reaction solution is evaporated, and the residue is taken up using ethyl acetate and washed with aq. citric acid, aq. sodium hydrogencarbonate solution and sat. aq. sodium chloride solution, dried over sodium sulfate, filtered and concentrated to dryness. The residue is chromatographed on silica gel using ethyl acetate/cyclohexane 1/2. 1.51 g (56% of th.) of the product are obtained.

後処理

  1. stirringit is stirred at room temperature for 18 h
  2. customThe reaction solution is evaporated
  3. washwashed with aq. citric acid, aq. sodium hydrogencarbonate solution and sat. aq. sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue is chromatographed on silica gel
  8. custom1.51 g (56% of th.) of the product are obtained

出典と根拠

ORDレコード
ord-6ec2906cbcb043bd9e21265ab3d5278a
出典データセット
uspto-grants-2008_07
特許番号
US07405201B2

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