2-Methyl-2-butene → HCID 22676800, compound

HRID 1006260Notes

Reaction equation

HRID 1006260 reaction equation
CC(=CC)C.OP([O-])(O)=O.[Na+].Cl([O-])(=O)(=O)=[O:13].[Na+].[CH:18]1([CH2:21][O:22][C:23]2[CH:24]=[C:25]([C:29]3[C:37]4[C:32](=[CH:33][CH:34]=[C:35]([CH2:38][CH:39]=[O:40])[CH:36]=4)[N:31]([CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[C:44]([O:48][CH3:49])[CH:43]=4)[C:30]=3[C:50]([O:52][CH2:53][CH3:54])=[O:51])[CH:26]=[CH:27][CH:28]=2)[CH2:20][CH2:19]1>C(O)(C)(C)C.O.C(OCC)(=O)C>[CH:18]1([CH2:21][O:22][C:23]2[CH:24]=[C:25]([C:29]3[C:37]4[C:32](=[CH:33][CH:34]=[C:35]([CH2:38][C:39]([OH:13])=[O:40])[CH:36]=4)[N:31]([CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[C:44]([O:48][CH3:49])[CH:43]=4)[C:30]=3[C:50]([O:52][CH2:53][CH3:54])=[O:51])[CH:26]=[CH:27][CH:28]=2)[CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 522606Sodium PerchlorateHCID 22676760HCID 22676760, compoundHCID 23672064Monosodium phosphate

Product 1

HCID 22676800HCID 22676800, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl-2-butene (2 mL), sodium phosphate monobasic (307 mg, 2.6 mmol) and sodium perchlorate (307 mg, 3.4 mmol) were added to a stirred solution of ethyl 3-[3-(cyclopropylmethoxy)phenyl]-1-(3-methoxybenzyl)-5-(2-oxoethyl)-1H-indole-2-carboxylate (Example 138, 169 mg, 0.34 mmol) in tert-butanol (8 mL) and water (3 mL). The reaction was stirred for 24 h and then diluted with ethyl acetate (100 mL). The solution was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. Flash chromatography of the residue over silica gel using 60% ethyl acetate/hexane afforded 35 mg (20%) of the product. The product had: 1H NMR (300 MHz, acetone-D6) δ 6.96-7.57 (m, 8 H), 6.58-6.80 (m, 3 H), 5.83 (s, 2 H), 4.11 (q, 2 H), 3.90 (d, 2 H), 3.70 (s, 3 H), 3.67 (s, 2 H), 1.24-1.40 (m, 1 H), 1.03 (t, 3 H), 0.55-0.65 (m, 2 H), 0.35-0.46 (m, 2 H); mass spectroscopy gave M−H+=512.5 (calc'd exact mass for C31H31NO6=513.22).

Workup

  1. washThe solution was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1c4b29435e349fa8defcb7ad08e2ae0
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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