Triethylamine → (E)-2-Acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acrylic Acid Methyl Ester

HRID 660629Notes

Reaction equation

HRID 660629 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[NH:19][C:18](=[O:23])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][O:25][C:26](=[O:33])[C:27]([NH:29][C:30](=[O:32])[CH3:31])=[CH2:28].C(N(CC)CC)C>CC#N.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:24][O:25][C:26](=[O:33])/[C:27](/[NH:29][C:30](=[O:32])[CH3:31])=[CH:28]\[C:13]1[CH:12]=[CH:11][C:10]([N:16]2[CH2:17][C:18](=[O:23])[NH:19][S:20]2(=[O:22])=[O:21])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 98644Methyl 2-acetamidoacrylateHCID 688386435-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Product 1

HCID 68838965(E)-2-Acetylamino-3-[3-benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acrylic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (200 mg, 0.4 mmol), 2-acetylaminoacrylic acid methyl ester (16.6 mg, 0.54 mmol), triethylamine (0.75 mL, 5.4 mmol) and Pd(OAc)2 (15 mg) in MeCN (5 mL) in a pressure vessel is heated at 100° C. for 18 h. The mixture is filtered and the solvent is removed under reduced pressure to give the title compound which is used directly in the next step.

Workup

  1. filtrationThe mixture is filtered
  2. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-9e2d5315ee284fd3936a73ffcd87d93e
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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