HCID 69922970, compound → HCID 54494954, compound

HRID 843153Notes

Reaction equation

HRID 843153 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[C@H:10]([CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[O:9][C:8]([C:18]2[O:19][C:20]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][CH2:30][CH2:31][N:32]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:33][C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)[C:21]=3[C:22]=2[CH3:23])=[N:7]1)=[O:5])[CH3:2]>C1(C)C=CC=CC=1.O.OO.[Ni]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:18]2[O:19][C:20]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][CH2:30][CH2:31][N:32]([C:40]([O:42][C:43]([CH3:44])([CH3:46])[CH3:45])=[O:41])[CH2:33][C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)[C:21]=3[C:22]=2[CH3:23])[O:9][C:10]=1[CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 69922970HCID 69922970, compound

Product 1

HCID 54494954HCID 54494954, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 7131114086676-91-7CatalystHCID 1140TolueneSolvent

Procedure

5-Cyclohexylmethyl-2-(3-methyl-4-{3-[tert-butoxycarbonyl-(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-yl)-trans-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester (10.0 mg) and nickel peroxide hydrate (22 mg) in toluene (2 ml) was heated at 80° C. under the atmosphere of argon for 23 hours. The reaction mixture was directly poured onto silica gel column chromatography and eluted with 2:3 mixture of n-hexane and ethyl acetate to give 5-cyclohexylmethyl-2-(3-methyl-4-{3-[tert-butoxycarbonyl-(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-yl)-oxazole-4-carboxylic acid ethyl ester (2.2 mg). FAB-MS: m/z 632 (MH+).

Workup

  1. additionThe reaction mixture was directly poured onto silica gel column chromatography
  2. washeluted with 2:3 mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-49165c7ca68f4a269cbf4113577cc76e
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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