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

HRID 891043Notes

Reaction equation

HRID 891043 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), 7.587.15 (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-6c271793a53e4a47bb9f1def591e56ec
Source dataset
uspto-grants-2006_02
Patent number
US07001921B1

Reaction notes

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