HCID 68495497, compound → HCID 76726990, compound

HRID 1822473Notes

Reaction equation

HRID 1822473 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16][N:15]2[C:38](=[O:52])[NH:39][CH:40]([C:48]([O:50][CH3:51])=[O:49])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]C=C)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]>ClCCl>[CH3:51][O:50][C:48]([CH:40]1[NH:39][C:38](=[O:52])[N:15]2[CH:14]([CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16]2)[C:12](=[O:13])[NH:11][C:6]2([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]([CH2:8]2)[CH:9]=[CH:10][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1)=[O:49]

Participants

3

Reactant 1

HCID 68495497HCID 68495497, compound

Product 1

HCID 76726990HCID 76726990, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 127 (170 mg, 0.2385 mmol) was dissolved in dichloromethane (40 ml) and degassed by bubbling nitrogen for 20 min. Hoveyda-Grubbs catalyst II generation (10 mg, 0.016 mmol, 6.7 mol %) was then added and the mixture was refluxed under nitrogen atmosphere overnight. The solvent was then evaporated, catalyst and salts were removed by flash chromatography (5% methanol in chloroform) and the crude product (120 mg, 73% yield, 85-90% purity) was used in next step MS (M+H+) 685

Workup

  1. customdegassed
  2. customby bubbling nitrogen for 20 min
  3. additionHoveyda-Grubbs catalyst II generation (10 mg, 0.016 mmol, 6.7 mol %) was then added
  4. temperaturethe mixture was refluxed under nitrogen atmosphere overnight
  5. customThe solvent was then evaporated
  6. customcatalyst and salts were removed by flash chromatography (5% methanol in chloroform)

Sources & evidence

ORD record
ord-c648f27f17f94e719b38c4f8c2edad85
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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