Di-tert-butyl dicarbonate → (E)-3-(2-tert-Butoxycarbonylamino-4-chlorophenyl)-acrylic acid methyl ester

HRID 1991047Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[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]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[NH:13][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:15]

Participants

Conditions

Temperature: 100 °C

Procedure

(E)-3-(2-Amino-4-chlorophenyl)-acrylic acid methyl ester (Carling, Robert W.; et al. J. Med. Chem. (1993), 36(22), 3397-408) (3.3 g, 15.6 mmol) in THF (63 ml) was combined with (BOC)2O (6.8 g, 31.2 mmol) and refluxed for 4 hours. THF was evaporated and a second portion of (BOC)2O added (6.8 g, 31.2 mmol). The mixture was heated to 100° C. for 18 hours. Recrystallisation from TBME/hexanes rendered the title compound as colorless crystals (4.6 g; 94%).

Workup

temperaturerefluxed for 4 hours
customTHF was evaporated
additiona second portion of (BOC)2O added (6.8 g, 31.2 mmol)
customRecrystallisation from TBME/hexanes

Sources & evidence

ORD record: ord-f2075763a3fe4051a2fd5f836228801f
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645760B2

Reaction notes

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