Hydrochloric Acid → HCID 57786524、化合物

HRID 253599

反応式

HRID 253599 の反応式
Cl.[NH2:2][C@@H:3]([CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C@H:4]([OH:9])[CH2:5][N:6]=[N+:7]=[N-:8].[CH3:17][O:18][C:19]1[C:20](=O)[C:21](=[O:25])[C:22]=1[O:23]C.C(N(CC)CC)C>C(#N)C>[N:6]([CH2:5][C@@H:4]([OH:9])[C@@H:3]([NH:2][C:20]1[C:21](=[O:25])[C:22](=[O:23])[C:19]=1[O:18][CH3:17])[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[N+:7]=[N-:8]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 57462034HCID 57462034、化合物

生成物 1

HCID 57786524HCID 57786524、化合物収率 65.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

The HCl salt of (2R,3S)-3-amino-1-azido-4-cyclohexylbutan-2-ol (˜74 mg, 0.30 mmol) and 3,4-dimethoxycyclobut-3-ene-1,2-dione (70 mg, 0.49 mmol) were dissolved in acetonitrile (3 mL). Triethylamine (84 μL, 0.60 mmol) was added. The reaction was stirred at rt for 4 h. The solvent was evaporated and the crude material was redissolved in CH2Cl2. The solution was washed with 2% aq HCl, followed by brine, and dried over Na2SO4. The solution was filtered and the solvent removed under reduced pressure. The crude material was purified by flash chromatography on silica gel eluting with hexanes/EtOAc. 3-((2S,3R)-4-Azido-1-cyclohexyl-3-hydroxybutan-2-ylamino)-4-methoxycyclobut-3-ene-1,2-dione (63 mg) was isolated as a solid; MS m/z 323.

後処理

  1. customThe solvent was evaporated
  2. dissolutionthe crude material was redissolved in CH2Cl2
  3. washThe solution was washed with 2% aq HCl
  4. dry with materialdried over Na2SO4
  5. filtrationThe solution was filtered
  6. customthe solvent removed under reduced pressure
  7. customThe crude material was purified by flash chromatography on silica gel eluting with hexanes/EtOAc

出典と根拠

ORDレコード
ord-6d1c67a960744597a83df4fab35c423e
出典データセット
uspto-grants-2011_01
特許番号
US07872028B2

関連ノート

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