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 1968907노트

반응식

HRID 1968907 반응식
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

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 9609Ethyl sulfideHCID 31398ChlorosuccinimideHCID 92727Lopinavir

생성물 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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-10 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-71fe7e6af3c44cf08de9c42c89a8c1f1
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426388B2

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