Diisopropylamine → (r)-5-[2-(4-Fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrol-1-yl]-3-hydroxy-1-pentanoic acid, (s)-2-hydroxy-1,2,2-triphenylethyl ester

HRID 2216505

反応式

HRID 2216505 の反応式
[CH3:1][C:2]([O:4][C@H:5]([C:12]([OH:25])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[Li+].CC([N-]C(C)C)C.C(NC(C)C)(C)C.[F:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[N:52]([CH2:53][CH2:54][CH:55]=[O:56])[C:51]([CH:57]([CH3:59])[CH3:58])=[C:50]([C:60]([NH:62][C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)=[O:61])[C:49]=2[C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)=[CH:44][CH:43]=1>C1COCC1.O.CC(O)=O>[F:41][C:42]1[CH:43]=[CH:44][C:45]([C:48]2[N:52]([CH2:53][CH2:54][C@@H:55]([OH:56])[CH2:1][C:2]([O:4][C@@H:5]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]([OH:25])([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:3])[C:51]([CH:57]([CH3:59])[CH3:58])=[C:50]([C:60]([NH:62][C:63]3[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=3)=[O:61])[C:49]=2[C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)=[CH:46][CH:47]=1

参加物

8

反応物 4

HCID 7912DiisopropylamineHCID 7360481,2-Ethanediol, 1,1,2-triphenyl-, 2-acetate, (2S)-HCID 2724682Lithium diisopropylamideHCID 113055725-(4-Fluorophenyl)-2-(1-methylethyl)-1-(3-oxopropyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide

生成物 1

HCID 11193615(r)-5-[2-(4-Fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrol-1-yl]-3-hydroxy-1-pentanoic acid, (s)-2-hydroxy-1,2,2-triphenylethyl ester

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

To a suspension of S-(−)-2-Hydroxy-1,2,2-triphenylethyl acetate (40.2 g) in 300 mL anhydrous THF at −10 to 0° C. was added a solution of LDA prepared by reaction of diisopropylamine (46.5 mL) with 2.5 M n-BuLi/hexanes (97 mL) in 300 mL anhydrous THF at −5 to 0° C. After stirring at 0° C. for 30 min the mixture was cooled to −78° C. Then, a solution of 5-(4-fluorophenyl)-2-(1-methylethyl)-1-(3-oxopropyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide 1 (50 g) in 280 mL anhydrous THF was added dropwise and maintained at −78° C. for 30 min. After adding 25 mL AcOH and 250 mL water the mixture was allowed to warm to room temperature. The layers were separated and the organic layer was washed and dried. After evaporation of the solvent the crude product was obtained (94 g). Analytical data are consistent with that from the prior art.

後処理

  1. temperaturewas cooled to −78° C
  2. temperaturemaintained at −78° C. for 30 min
  3. temperatureto warm to room temperature
  4. customThe layers were separated
  5. washthe organic layer was washed
  6. customdried
  7. customAfter evaporation of the solvent the crude product
  8. customwas obtained (94 g)

出典と根拠

ORDレコード
ord-9776c7f32cee4957a73dc3174f7a7934
出典データセット
uspto-grants-2006_09
特許番号
US07112604B2

関連ノート

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