Sodium triacetoxyborohydride → HCID 67316393、化合物

HRID 1013819

反応式

HRID 1013819 の反応式
C([C@@H:8]1COC(=O)[N:9]1[C:14](=[O:36])[C@H:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:22][C:21]=1[Cl:35])[CH2:16]C=O)C1C=CC=CC=1.[NH:37]1[C:45]2[CH:44](N)[CH2:43][CH2:42][CH2:41][C:40]=2[CH:39]=[N:38]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(#N)C>[CH2:28]([O:27][C:23]1[CH:22]=[C:21]([Cl:35])[C:20]([CH2:19][C@@H:15]2[CH2:16][CH2:8][N:9]([CH:44]3[C:45]4[NH:37][N:38]=[CH:39][C:40]=4[CH2:41][CH2:42][CH2:43]3)[C:14]2=[O:36])=[C:25]([Cl:26])[CH:24]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

参加物

6

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 219419624,5,6,7-tetrahydro-1H-indazol-7-amineHCID 59515429(R)-4-((R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde

生成物 1

HCID 67316393HCID 67316393、化合物収率 28%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

Add a solution of (R)-4-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde, Preparation 38, (9.95 g, 18.9 mmol) in CH2Cl2 (300 mL) to a solution of 4,5,6,7-tetrahydro-1H-indazol-7-ylamine (2.60 g, 19.00 mmol) in acetonitrile (300 mL) and stir for 30 minutes at room temperature under N2. Add sodium triacetoxyborohydride (12.02 g, 56.9 mmol) to the reaction and stir for 72 hours. Remove the solvent in vacuo and extract solid with ethyl acetate, water and saturated NaHCO3. Dry the organic layer (Na2SO4), filter and concentrate under vacuum. Purify the residue by silica gel chromatography with a gradient of 0 to 10% methanol in CH2Cl2 to afford 2.53 g (28%) of the title compound. MS (m/z): 470 (M+).

後処理

  1. additionAdd
  2. stirringstir for 72 hours
  3. customRemove the solvent in vacuo
  4. extractionextract solid with ethyl acetate, water and saturated NaHCO3
  5. dry with materialDry the organic layer (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify the residue by silica gel chromatography with a gradient of 0 to 10% methanol in CH2Cl2

出典と根拠

ORDレコード
ord-a7448ea71a5743dbafc3e9a0aab1a6db
出典データセット
uspto-grants-2011_07
特許番号
US07981918B2

関連ノート

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