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

HRID 2351816ノート

反応式

HRID 2351816 の反応式
[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

参加物

11

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 5

HCID 241Benzene溶媒HCID 679Dimethyl Sulfoxide溶媒3 回HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-a8d943b02517429b976ed50313026b7a
出典データセット
uspto-grants-1989_10
特許番号
US04873339

反応ノート

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