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HRID2284874

反应详情

EQUATION

反应方程式

HRID 2284874 的结构方程式

REACTANTS

反应物

4
结构：CCN(C(C)C)C(C)C
HCID81531

Diisopropylethylamine

C8H19N

结构：C[O-].[Na+]
HCID10942334

Methanol, sodium salt

CH3NaO

结构：CC(C)CNC(=O)NCC(=O)N1CCC2(CCCNC2)CC1
HCID118021368

未命名化合物

结构：CC(=O)OC[C@H]1O[C@@H](n2cc(Cc3ccc(OCCCOS(C)(=O)=O)cc3)c3c(C)cccc32)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
HCID118045083

未命名化合物

PRODUCTS

生成物

1
结构：Cc1cccc2c1c(Cc1ccc(OCCCN3CCCC4(CCN(C(=O)CNC(=O)NCC(C)C)CC4)C3)cc1)cn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
HCID91755010

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CO
溶剂HCID887

Methanol

CH4O

结构：CC#N
溶剂HCID6342

Acetonitrile

C2H3N

CONDITIONS

反应条件

温度
80 °C

PROCEDURE

实验过程

To a 0.25 L round bottom flask add [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[4-methyl-3-[[4-(3-methylsulfonyloxypropoxy)phenyl]methyl]indol-1-yl]tetrahydropyran-2-yl]methyl acetate (7.2 g, crude), 1-[2-(4,9-diazaspiro[5.5]undecan-9-yl)-2-oxo-ethyl]-3-isobutyl-urea (12.28 mmol), acetonitrile (100 mL), and diisopropylethylamine (40.92 mmol). Heat at 80° C. for 16 hours then concentrate under reduced pressure. Add methanol (50 mL) and sodium methoxide (20.46 mmol, 30% solution in MeOH) and stir at room temperature for 1 hour. Quench by adding a small piece of dry ice. Concentrate under reduced pressure. Purify by reverse phase flash chromatography (400 g C18 cartridge) eluting with 5-80% water (0.1% formic acid) in acetonitrile (0.1 % formic acid) in three portions. Concentrate under reduced pressure to yield the title compound as a formic acid salt containing small impurities. Dissolve the salt in 7N ammonia in methanol (20 mL) then concentrate to form the free base. Purify the free base by flash chromatography (330 g silica gel cartridge) eluting with 5% 7N ammonia in methanol/dichloromethane. Concentrate the product fractions under reduced pressure to yield the title compound (1.75 g, 22.81%): MS (m/z): 746.6 (M+H). H1 NMR (400.31 MHz, CD3OD): δ 7.28 (d, J=8.4 Hz, 1H), 7.03 (d, J=8.4 Hz, 2H), 7.02 (s, 1H), 6.97 (t, J=8.8 Hz, 1H), 6.69 (d, J=7.2 Hz, 1H), 5.37 (d, J=9.2 Hz, 1H), 4.15 (s, 2H), 3.95 (t, J=6.0 Hz, 2H), 3.91 (d, J=1.6 Hz, 2H), 3.87-3.80 (m, 2H), 3.65 (dd, J=11.6, 5.6 Hz, 1H), 3.57-3.38 (m, 5H), 3.31 (bm, 2H), 2.90 (d, J=6.8 Hz, 2H), 2.46-2.13 (m, 8H), 1.88 (pentet, J=6.8 Hz, 2H), 1.68 (septet, J=6.8 Hz, 1H), 1.61-1.28 (m, 8H), 0.86 (d, J=6.8, 6H).

WORKUP

后处理

  1. concentrationthen concentrate under reduced pressure
  2. customQuench
  3. additionby adding a small piece of dry ice
  4. concentrationConcentrate under reduced pressure
  5. customPurify by reverse phase flash chromatography (400 g C18 cartridge)
  6. washeluting with 5-80% water (0.1% formic acid) in acetonitrile (0.1 % formic acid) in three portions
  7. concentrationConcentrate under reduced pressure