Hydrochloric Acid → (3aS,6aR)-hexahydro-1-[(R)-(1-phenylethyl)]-2-oxo-3-benzylthieno[3,4-d]imidazol-4-ylidene pentanoic acid

HRID 232444

반응식

HRID 232444 반응식
[H-].[Na+].[H][H].[Br-].[C:6]([CH2:9][CH2:10][CH2:11][CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:8])=[O:7].[C:32]1([C@H:38]([N:40]2[C@H:44]3[CH2:45][S:46][C:47](=O)[C@H:43]3[N:42]([CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:41]2=[O:56])[CH3:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl>CS(C)=O.C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC=CC=1.O>[C:32]1([C@H:38]([N:40]2[C@H:44]3[CH2:45][S:46][C:47](=[C:9]([CH2:10][CH2:11][CH3:12])[C:6]([OH:8])=[O:7])[C@H:43]3[N:42]([CH2:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[C:41]2=[O:56])[CH3:39])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

참가 물질

11

반응물 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 11013605(3aS,6aR)-1-[(R)-(1-phenylethyl)]-3-benzyl-dihydro-1H-thieno[3,4-d]-imidazol-2,4(3H,3aH)-dioneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 86743268(3aS,6aR)-hexahydro-1-[(R)-(1-phenylethyl)]-2-oxo-3-benzylthieno[3,4-d]imidazol-4-ylidene pentanoic acid

시약·촉매·용매 5

HCID 241Benzene용매HCID 679Dimethyl Sulfoxide용매3회HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

159.8 mg (3.66 mmol) of sodium hydride and 1.7 ml of dimethyl sulfoxide were placed in a 25-ml round-bottom flask. The suspension was heated with stirring and under argon to 70° C. It was stirred for 40 minutes more until evolution of hydrogen was complete. The solution was cooled to room temperature and a solution of 801.5 mg (1.8 mmol) of (4-carboxybutyl)-triphenylphosphonium bromide in 1 ml of dimethyl sulfoxide was added. The dark red reaction mixture was stirred for 15 minutes and then added dropwise to a solution of 271 mg (0.77 mmol) of (3as,6aR)-1-[(R)-(1-phenylethyl)]-3-benzyl-dihydro-1H-thieno[3,4-d]-imidazol-2,4(3H,3aH)-dione in 2 ml of dimethyl sulfoxide and 0.2 ml of toluene. The reaction mixture was stirred for 2 hours at room temperature. Then 1 g of ice, 1 ml of conc, HCl and again 9 g of ice were added. After 5 minutes, 5 ml of water, 10 ml of benzene and 5 ml of ethyl acetate were added. Then the mixture was stirred for 1 hour at 60° C. The phases were separated. The brown organic phase was dried with 5 g of magnesium sulfate and separated with 4 preparative silica gel thin-layer plates (1 mm) by means of ethyl acetate. The product, (3aS, 6aR)-hexahydro-1-[(R)-(1-phenylethyl)]-2-oxo-3-benzylthieno[3,4-d]-imidazol-4-ylidene pentanoic acid, a colorless oil, was obtained in a yield of 38.2 mg (12 percent). Concerning the product:

후처리

  1. temperatureThe suspension was heated
  2. temperatureThe solution was cooled to room temperature
  3. customThe dark red reaction mixture
  4. stirringwas stirred for 15 minutes
  5. stirringThe reaction mixture was stirred for 2 hours at room temperature
  6. stirringThen the mixture was stirred for 1 hour at 60° C
  7. customThe phases were separated
  8. dry with materialThe brown organic phase was dried with 5 g of magnesium sulfate
  9. customseparated with 4 preparative silica gel thin-layer plates (1 mm) by means of ethyl acetate

출처 및 근거

ORD 기록
ord-a739537c732e46d2b401686ea9f762a8
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851540

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