Acetyl chloride → (R)-3-((S)-1-acetylpyrrolidin-3-yl)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)propanamide

HRID 594824노트

반응식

HRID 594824 반응식
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([C@@H:13]([CH2:23][C@H:24]3[CH2:28][CH2:27][NH:26][CH2:25]3)[C:14]([NH:16][C:17]3[S:18][C:19]([F:22])=[CH:20][N:21]=3)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37]>ClCCl>[C:36]([N:26]1[CH2:27][CH2:28][C@H:24]([CH2:23][C@H:13]([C:10]2[CH:9]=[CH:8][C:7]([S:4]([CH:1]3[CH2:3][CH2:2]3)(=[O:5])=[O:6])=[CH:12][CH:11]=2)[C:14]([NH:16][C:17]2[S:18][C:19]([F:22])=[CH:20][N:21]=2)=[O:15])[CH2:25]1)(=[O:38])[CH3:37]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 118268346(R)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)-3-((S)-pyrrolidin-3-yl)propanamide

생성물 1

HCID 73506953(R)-3-((S)-1-acetylpyrrolidin-3-yl)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)propanamide수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The (R)-2-(4-(cyclopropylsulfonyl)phenyl)-N-(5-fluorothiazol-2-yl)-3-((S)-pyrrolidin-3-yl)propanamide (1.17 g, 2.77 mmol) obtained in Step 1 of Example 2 was dissolved in dichloromethane (27 mL), and thereafter, triethylamine (0.806 mL, 5.81 mmol) and acetyl chloride (0.207 mL, 2.91 mmol) were added to the above obtained solution under ice-cold condition. The obtained mixture was stirred for 20 minutes. Thereafter, the reaction solution was washed with a 1 M aqueous solution of hydrochloric acid and a saturated aqueous solution of sodium hydrogen carbonate. The resultant was dried over anhydrous sodium sulfate, and was then concentrated in vacuo. The obtained residue was purified by silica gel chromatography (chloroform/methanol=1%→15%) to obtain the captioned compound (980 mg, 76%) in the form of a white solid.

후처리

  1. washThereafter, the reaction solution was washed with a 1 M aqueous solution of hydrochloric acid
  2. dry with materialThe resultant was dried over anhydrous sodium sulfate
  3. concentrationwas then concentrated in vacuo
  4. customThe obtained residue was purified by silica gel chromatography (chloroform/methanol=1%→15%)

출처 및 근거

ORD 기록
ord-0434815c3af74ad9bc55e90822fa12df
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242978B2

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