Hydrochloric Acid → HCID 57786524, 화합물

HRID 253599

반응식

HRID 253599 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 57786524HCID 57786524, 화합물수율 65.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6d1c67a960744597a83df4fab35c423e
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872028B2

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