Triethylamine → (2s)-n-{(1s,3s,4s)-1-Benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-[1-(ethylthio)ethoxy]-5-phenylpentyl}-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanamide

HRID 1968907ノート

反応式

HRID 1968907 の反応式
ClN1C(=O)CCC1=O.[CH2:9]([S:11][CH2:12][CH3:13])[CH3:10].[CH2:14]([C@H:21]([NH:46][C:47](=[O:59])[C@@H:48]([N:52]1[CH2:57][CH2:56][CH2:55][NH:54][C:53]1=[O:58])[CH:49]([CH3:51])[CH3:50])[CH2:22][C@H:23]([OH:45])[C@@H:24]([NH:32][C:33](=[O:44])[CH2:34][O:35][C:36]1[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:37]=1[CH3:43])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>O1CCCC1>[CH2:14]([C@H:21]([NH:46][C:47](=[O:59])[C@@H:48]([N:52]1[CH2:57][CH2:56][CH2:55][NH:54][C:53]1=[O:58])[CH:49]([CH3:51])[CH3:50])[CH2:22][C@H:23]([O:45][CH:9]([S:11][CH2:12][CH3:13])[CH3:10])[C@@H:24]([NH:32][C:33](=[O:44])[CH2:34][O:35][C:36]1[C:37]([CH3:43])=[CH:38][CH:39]=[CH:40][C:41]=1[CH3:42])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 9609Ethyl sulfideHCID 31398ChlorosuccinimideHCID 92727Lopinavir

生成物 1

HCID 42637794(2s)-n-{(1s,3s,4s)-1-Benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-[1-(ethylthio)ethoxy]-5-phenylpentyl}-3-methyl-2-(2-oxotetrahydropyrimidin-1(2h)-yl)butanamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-10 °C

実験手順

A slurry of N-chlorosuccinimide (6.5 g, 48.7 mmol) in tetrahydrofuran (50 mL) was cooled to −10° C., followed by addition of diethyl sulfide (7.0 mL) and then by addition of a solution of Example 3 (5.0 g) in tetrahydrofuran (20 mL). A solution of triethylamine (9.0 mL) in tetrahydrofuran (15 mL) was then added dropwise and the mixture was stirred at −10° C. for 1.5 h. The reaction was quenched with 10% Na2CO3 and extracted twice with ethyl acetate. The combined organic was washed with water and brine and dried over MgSO4, filtered and evaporated to give the crude product (7.5 g).

後処理

  1. customThe reaction was quenched with 10% Na2CO3
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-71fe7e6af3c44cf08de9c42c89a8c1f1
出典データセット
uspto-grants-2013_04
特許番号
US08426388B2

反応ノート

読み込み中…