Hydrochloric Acid → HCID 23511825, compound

HRID 354297Notes

Reaction equation

HRID 354297 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:30])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]CC2C=CC=CC=2)=[O:19])=[CH:13][C:12]=1[O:28][CH3:29].[OH-].[Na+].Cl>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:30])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][C:12]=1[O:28][CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23512303benzyl 4-[N'-(2-fluorophenyl)ureido]-3-methoxyphenylacetate

Product 1

HCID 23511825HCID 23511825, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of benzyl 4-[N′-(2-fluorophenyl)ureido]-3-methoxyphenylacetate (2.04 g, 5 mmol) in THF (40 mL) was added 0.25 N NaOH (40 mL). The resulting mixture was stirred overnight. The mixture was poured into 1 N HCl (10 mL), and the resulting precipitate was collected with suction. The residue was recrystallized from CHCl3—EtOH to give 1.04 g (66%) 4-[N′-(2-fluorophenyl)ureido]-3-methoxyphenylacetic acid as a white crystalline powder. mp 185-188 (d); 1H-NMR (DMSO-d6) δ3.50 (2H, s), 3.82 (3H, s), 6.78 (1H, dd, J=1.4 and 8.3 Hz), 6.92 (1H, d, J=1.4 Hz), 6.95-7.01 (1H, m), 7.10-7.14 (1H, m), 7.19-7.24 (1H, m), 8.01 (1H, d, J=8.3 Hz), 8.14-8.18 (1H, m), 8.72 (1H, s), 9.17 (1H, s); MS (FAB) m/z 319 (M++1); Anal. Calcd. for C16H15N2O4F: C, 60.37; H, 4.75; N, 8.80. Found: C, 60.20; H, 4.82; N, 8.67.

Workup

  1. customthe resulting precipitate was collected with suction
  2. customThe residue was recrystallized from CHCl3—EtOH

Sources & evidence

ORD record
ord-ade5f67ed8e4408086b0129b6efd712b
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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