三乙酰氧基硼氢化钠 → HCID 67317121，化合物

HRID 1013822

反应方程式

HRID 1013822 反应方程式
C([C@@H]1COC(=O)N1[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][CH:17]=O)C1C=CC=CC=1.[NH:37]1[C:45]2[CH2:44][CH:43]([NH2:46])[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][CH2:17][N:46]([CH:43]3[CH2:44][C:45]4[NH:37][N:38]=[CH:39][C:40]=4[CH2:41][CH2:42]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

参与物

6

反应物 3

HCID 5049666三乙酰氧基硼氢化钠HCID 128984204,5,6,7-四氢-1H-吲唑-6-胺HCID 59515429(R)-4-((R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde

产物 1

HCID 67317121HCID 67317121，化合物收率 54%

试剂、催化剂与溶剂 2

HCID 6342乙腈溶剂HCID 6344二氯甲烷溶剂

实验过程

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, (8.17 g, 15.5 mmol) in CH2Cl2 (100 mL) to a solution of 4,5,6,7-tetrahydro-1H-indazol-6-ylamine (2.13 g, 15.5 mmol) in acetonitrile (200 mL) and stir for 30 minutes at room temperature under N2. Add sodium triacetoxyborohydride (9.89 g, 46.7 mmol) to the reaction and stir for 18 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 3.93 g (54%) of the title compound. MS (m/z): 470 (M+).

后处理

  1. additionAdd
  2. stirringstir for 18 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

来源与证据

ORD记录
ord-94f60d92b451432b85aa7e1333db4d8c
来源数据集
uspto-grants-2011_07
专利号
US07981918B2

关联笔记

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