{9-[(3-Phenoxyphenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, tert-butyl ester → {9-[(3-Phenoxyphenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid

HRID 51370Notes

Reaction equation

HRID 51370 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][N:15]2[C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([O:28][CH2:29][C:30]([O:32]C(C)(C)C)=[O:31])[C:22]=3[C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][C:20]=3[C:37](=[O:39])[NH2:38])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][N:15]2[C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([O:28][CH2:29][C:30]([OH:32])=[O:31])[C:22]=3[C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][C:20]=3[C:37](=[O:39])[NH2:38])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86756262{9-[(3-Phenoxyphenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, tert-butyl ester

Product 1

HCID 9869143{9-[(3-Phenoxyphenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acidYield 112%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the {9-[(3-phenoxyphenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, tert-butyl ester (30.0 mg, 0.063 mM) in 2 mL of trifluoroacetic acid was stirred at room temperature for 6 hours. The solvent was removed in vacuo. The residue was dried in vacuo to afford 30.0 mg (100%) of the {9-[(3-phenoxyphenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid as a white powder. 1H NMR (DMSO-d6) δ13.0 (br s, 1H), 7.75 (s, 1H), 7.6 (d, 1H, J=8 Hz), 7.5-6.8 (m, 14H), 6.6 (d, 1H, J=8 Hz), 5.7 (s, 2H), and 4.8 (s, 2H). IR (KBr, cm−1) 3450, 3400, 1740, 1651, 1592, 1585, 1487, 1457, 1441, 1329, 1250, and 1158. MS (ES) m/e 465, 467.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-fba974386de84557abef9bc42e1b2701
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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