HCID 21915179, compound → HCID 21915037, compound

HRID 2117953Notes

Reaction equation

HRID 2117953 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7](/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].C(NC1SC(/C=C\C(OCC)=O)=C(CCC2C=CC(NC(OC(C)(C)C)=O)=CC=2)N=1)(=O)C.[H][H]>[Pd].C1COCC1>[C:1]([NH:4][C:5]1[S:6][C:7]([CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 21915179HCID 21915179, compoundHCID 86595613HCID 86595613, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21915037HCID 21915037, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl(2E)-3-[2-(acetylamino)-4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}ethyl)-1,3-thiazol-5-yl]acrylate and ethyl(2Z)-3-[2-(acetylamino)-4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}ethyl)-1,3-thiazol-5-yl]acrylate (200 mg), THF (7 ml) and 10% Pd/C (392 mg) were combined under nitrogen atmosphere. The mixture was stirred under 3 atm hydrogen atmosphere at 20° C. for 3 h. The reaction mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo to give ethyl 3-[2-(acetylamino)-4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}ethyl)-1,3-thiazol-5-yl]propanoate as a colorless amorphous.

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-49bd51c990044aee8b992e615f9050a5
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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