Hydrochloric Acid → {(8R)-8-Methyl-3-{1-[4-(1,3-oxazol-2-yl)phenyl]cyclopropyl}-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-8-yl}methanol

HRID 1424133ノート

反応式

HRID 1424133 の反応式
[Si]([O:8][CH2:9][C@:10]1([CH3:34])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26]([C:29]5[O:30][CH:31]=[CH:32][N:33]=5)=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1)(C(C)(C)C)(C)C.Cl>CO>[CH3:34][C@@:10]1([CH2:9][OH:8])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:24]=[CH:25][C:26]([C:29]5[O:30][CH:31]=[CH:32][N:33]=5)=[CH:27][CH:28]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86712977(8R)-8-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-3-{1-[4-(1,3-oxazol-2-yl)phenyl]cyclopropyl}-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

生成物 1

HCID 86712978{(8R)-8-Methyl-3-{1-[4-(1,3-oxazol-2-yl)phenyl]cyclopropyl}-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-8-yl}methanol収率 88.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of the compound (674 mg, 1.36 mmol) obtained in Example 85-1) and 4 M hydrochloric acid (1,4-dioxane solution, 4 mL) in methanol (8 mL) was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, a 5 M aqueous sodium hydroxide solution (40 mL) was added to the residue, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel chromatography (ethyl acetate:methanol=20:80) to obtain the title compound (460 mg, 88%) as a yellow solid.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona 5 M aqueous sodium hydroxide solution (40 mL) was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. customthe residue was purified by silica gel chromatography (ethyl acetate:methanol=20:80)

出典と根拠

ORDレコード
ord-0934eb0c56114f55b496b124ef454279
出典データセット
uspto-grants-2015_01
特許番号
US08927536B2

反応ノート

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