t-Butyl 3-methoxy-4-phenylureidophenylacetate → HCID 22244728, compound

HRID 1358197Notes

Reaction equation

HRID 1358197 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11]>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:19][C:20]([OH:22])=[O:21])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11]

Participants

3

Reactant 1

HCID 22244715t-Butyl 3-methoxy-4-phenylureidophenylacetate

Product 1

HCID 22244728HCID 22244728, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of t-butyl 3-methoxy-4-phenylureidophenylacetate (0.108 g, 0.303 mmol) in trifluoroacetic acid (5.0 mL) was stirred for 30 min. The reaction was concentrated and the residue coevaporated with methylene chloride (2×) then ether to afford 3-methoxy-4-phenylureidophenylacetic acid (0.090 g, 99%) as a white foam: 1H NMR (CD3SOCD3, 300 MHz, ppm) 9.28 (s, 1H), 8.18 (s, 1H), 8.02 (d, 7.5 Hz, 1H), 7.58-7.15 (m, 5H), 6.91 (bm, 2H), 6.77 (d, 7.5 Hz, 1H), 3.85 (s, 3H), 3.49 (s, 2H).

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-10bb163de8c84a1cb64fd7190b7ac11a
Source dataset
uspto-grants-2003_07
Patent number
US06596687B1

Reaction notes

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