Di-tert-butyl dicarbonate → HCID 58683692, compound

HRID 1991056Notes

Reaction equation

HRID 1991056 reaction equation
[CH3:1][O:2][C:3](=[O:14])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[NH2:13].[O:15](C(OC(C)(C)C)=O)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=O>C1COCC1>[CH3:1][O:2][C:3](=[O:14])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[NH:13][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:15]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 23003224HCID 23003224, compound

Product 1

HCID 58683692HCID 58683692, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-3-(2-Amino-5-chlorophenyl)-acrylic acid methyl ester (Gonzalez-Zamora, Eduardo et al Chem. Comm. (2001), (17), 1684-1685.) (1.7 g, 8.0 mmol) in THF (6.5 ml) was combined with (BOC)2O (6.98 g9 32.0 mmol) and refluxed for 4 hours. THF was evaporated and the residue purified via chromatography (SiO2, acetone/hexanes 5/95) followed by recrystallisation from hexanes to yield the title compound as yellow crystals (1.8 g; 72%).

Workup

  1. temperaturerefluxed for 4 hours
  2. customTHF was evaporated
  3. customthe residue purified via chromatography (SiO2, acetone/hexanes 5/95)
  4. customfollowed by recrystallisation from hexanes

Sources & evidence

ORD record
ord-09839bebac294b148a42c59f140bd976
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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