Water → HCID 68491776, compound

HRID 1944209Notes

Reaction equation

HRID 1944209 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:14])([CH3:13])[NH:9][CH2:10]2)=[CH:5][C:4]=1[O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18].[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([O:39][CH3:40])[C:36]=1[O:37][CH3:38])[C:31](Cl)=[O:32].O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:13])([CH3:14])[N:9]([C:31]([C:30]3[CH:34]=[C:35]([O:39][CH3:40])[C:36]([O:37][CH3:38])=[C:28]([O:27][CH3:26])[CH:29]=3)=[O:32])[CH2:10]2)=[CH:5][C:4]=1[O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 68495874HCID 68495874, compound

Product 1

HCID 68491776HCID 68491776, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 225 (300 mg, 0.83 mmol) in DCM (5 ml) was added TEA (0.23 ml, 1.65 mmol) and 3,4,5-trimethoxybenzoyl chloride (228 ml, 0.99 mmol). The reaction mixture was stirred at rt for 12 h. Water (10 ml) was added and the aqueous layer was extracted with DCM (3×30 ml). The combined organic phases were washed with sat. aq. NaHCO3 (10 ml) and brine (10 ml), dried (MgSO4) and concentrated in vacuo. Purification (flashmaster: 20 g, gradient elution 100% hex to 100% EtOAc over 25 min) afforded the title compound (240 mg, 52%) as a colourless oil. 1H NMR (270 MHz; CDCl3) 1.04 (18H, d, J=6.7 Hz, 6×CH3CH), 1.14-1.24 (3H, m, 3×CH), 1.55 (6H, s, 2×CH3), 2.74 (2H, s, CH2), 3.80 (3H, s, OCH3), 3.85 (6H, s, 2×OCH3), 3.86 (3H, s, OCH3), 4.19 (2H, s, CH2), 6.53 (1H, s, CH), 6.56 (2H, s, 2×CH), 6.71 (1H, s, CH). LC/MS (ES+) tr=0.2.23 min, m/z 580.24 (M++Na). HRMS (ES+) calcd for C31H47NO6Si (M++H) 558.3245, found 558.3237.

Workup

  1. extractionthe aqueous layer was extracted with DCM (3×30 ml)
  2. washThe combined organic phases were washed with sat. aq. NaHCO3 (10 ml) and brine (10 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification (flashmaster: 20 g, gradient elution 100% hex to 100% EtOAc over 25 min)

Sources & evidence

ORD record
ord-2c66b190c8924534b057704d33ba1472
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

Loading…