Diethyl Ether → (S)-4-[4-[[7-(Aminosulfonyl)-6-chloro-3,4-dihydro-1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl]methyl]phenoxy]-1-[(S)-3-mercapto-2-methyl-1-oxopropyl]-L-proline

HRID 485327

반응식

HRID 485327 반응식
[NH2:1][S:2]([C:5]1[C:46]([Cl:47])=[CH:45][C:8]2[NH:9][CH:10]([CH2:15][C:16]3[CH:44]=[CH:43][C:19]([O:20][CH:21]4[CH2:25][N:24]([C:26](=[O:39])[C@H:27]([CH3:38])[CH2:28][S:29]C(=O)C5C=CC=CC=5)[C@H:23]([C:40]([OH:42])=[O:41])[CH2:22]4)=[CH:18][CH:17]=3)[NH:11][S:12](=[O:14])(=[O:13])[C:7]=2[CH:6]=1)(=[O:4])=[O:3].CCOCC.SC[C@@H](C)C(N1CCC[C@H]1C(O)=O)=O>C(O)(=O)C.CO.C(Cl)Cl>[NH2:1][S:2]([C:5]1[C:46]([Cl:47])=[CH:45][C:8]2[NH:9][CH:10]([CH2:15][C:16]3[CH:44]=[CH:43][C:19]([O:20][CH:21]4[CH2:25][N:24]([C:26](=[O:39])[C@H:27]([CH3:38])[CH2:28][SH:29])[C@H:23]([C:40]([OH:42])=[O:41])[CH2:22]4)=[CH:18][CH:17]=3)[NH:11][S:12](=[O:14])(=[O:13])[C:7]=2[CH:6]=1)(=[O:3])=[O:4]

참가 물질

7

반응물 3

HCID 3283Diethyl EtherHCID 44093CaptoprilHCID 13520532(S)-4-[4-[[7-(Aminosulfonyl)-6-chloro-3,4-dihydro-1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl]methyl]phenoxy]-1-[(S)-3-(benzoylthio)-2-methyl-1-oxopropyl]-L-proline

생성물 1

HCID 13520530(S)-4-[4-[[7-(Aminosulfonyl)-6-chloro-3,4-dihydro-1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl]methyl]phenoxy]-1-[(S)-3-mercapto-2-methyl-1-oxopropyl]-L-proline

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매2회HCID 6344Dichloromethane용매

실험 절차

The product from Example 1 (0.3 g., 0.4 mmole) is dissolved in 50 ml. of argon purged sodium hydroxide (2.5%) and stirred at 25° for 3 hours. The solution is acidified with 10% potassium bisulfate and extracted with ethyl acetate. The organics are dried (Na2SO4) and evaporated. Trituration with ether gives a solid. Chromatography on 50 g. of LH-20 in methanol and pooling and evaporation of the product containing fractions gives a glass. Trituration with ether gives 0.2 g. of (S)-4-[[7-(aminosulfonyl)-6-chloro-3,4-dihydro-1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl]methyl]phenoxy]-1-[(S)-3-mercapto-2-methyl-1-oxopropyl]-L-proline as a white crystalline solid; m.p. 175°-185°; [α]D =-22° (c=0.1%, methanol). TLC (silica, methylene chloride:methanol:acetic acid; 8:1:1) Rf =0.32.

후처리

  1. customof argon purged sodium hydroxide (2.5%)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organics are dried (Na2SO4)
  4. customevaporated
  5. customTrituration with ether gives a solid
  6. customof LH-20 in methanol and pooling and evaporation of the product
  7. additioncontaining fractions
  8. customgives a glass

출처 및 근거

ORD 기록
ord-f471b6e159d14687be22a860b7c8e2bf
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04536501

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