Toluene → HCID 66920056, compound

HRID 1908616Notes

Reaction equation

HRID 1908616 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:42])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([C:31]3[O:32]C=CC=3)[N:28]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2].I([O-])(=O)(=O)=[O:44].[Na+].C1(C)C=CC=CC=1>ClC(Cl)(Cl)Cl.C(#N)C.O.[Ru](Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:42])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([C:31]([OH:44])=[O:32])[N:28]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

8

Reactant 3

HCID 1140TolueneHCID 23667635Sodium periodateHCID 669200774-{(S)-4-tert-Butoxycarbonyl-2-[(5-furan-2-yl-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester

Product 1

HCID 66920056HCID 66920056, compound

Reagents, catalysts & solvents 4

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Procedure

To a vigorously stirred mixture of 320 mg of 4-{(S)-4-tert-Butoxycarbonyl-2-[(5-furan-2-yl-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester in 2 ml of tetrachloromethane, 2 ml of acetonitrile and 3 ml of water, 531 mg of sodium periodate and 1 mg of ruthenium(III)chloride was added at RT. After 1 h, 20 ml of toluene was added and the solvents were removed under reduced pressure. The crude product was used in the subsequent reaction. Yield: 314 mg.

Workup

  1. additionwas added at RT
  2. customthe solvents were removed under reduced pressure
  3. customThe crude product was used in the subsequent reaction

Sources & evidence

ORD record
ord-eeb84e6471ea4c9883806b48210eef5c
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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