Ethyl Acetate → HCID 54460231, compound

HRID 1789870Notes

Reaction equation

HRID 1789870 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C:5]([CH2:7][C:8]1[CH:9]=[N:10][C:11]([N:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[N:12][CH:13]=1)=[CH2:6])[CH3:2].CCOC(C)=O.[C:36]([OH:39])(=[S:38])[CH3:37]>>[CH2:1]([O:3][C:4](=[O:29])[CH:5]([CH2:6][S:38][C:36](=[O:39])[CH3:37])[CH2:7][C:8]1[CH:9]=[N:10][C:11]([N:14]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[N:12][CH:13]=1)[CH3:2]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 54446966HCID 54446966, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 54460231HCID 54460231, compoundYield 89%

Procedure

TEA (0.189 mL, 1.35 mmol) was added to a solution of 2-(2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin-5-ylmethyl)-acrylic acid ethyl ester (0.53 g, 1.30 mmol) in thioacetic acid (13 mL) at 0° C. under argon. The mixture was stirred at room temperature for 40 h. EtOAc was added and the solution was washed with Na2CO3 and brine, dried and concentrated under reduced pressure. Flash chromatography (heptane/EtOAc, 5:1→1:1) gave 2-acetylsulfanylmethyl-3-(2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin-5-yl)-propionic acid ethyl ester(0.56 g, 89%).

Workup

  1. washthe solution was washed with Na2CO3 and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8f9fbfea5534b4395cf10443b1c8de1
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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