Trifluoroacetic acid → 4-(6-Cyano-4-(methoxycarbonyl)-chroman-7-yloxy)benzoic acid

HRID 1626392Notes

Reaction equation

HRID 1626392 reaction equation
C([O:5][C:6]([C:8]1[CH:30]=[CH:29][C:11]([O:12][C:13]2[CH:22]=[C:21]3[C:16]([CH:17]([C:23]([O:25][CH3:26])=[O:24])[CH2:18][CH2:19][O:20]3)=[CH:15][C:14]=2[C:27]#[N:28])=[CH:10][CH:9]=1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:27]([C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:13]=1[O:12][C:11]1[CH:29]=[CH:30][C:8]([C:6]([OH:7])=[O:5])=[CH:9][CH:10]=1)[O:20][CH2:19][CH2:18][CH:17]2[C:23]([O:25][CH3:26])=[O:24])#[N:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67080240Methyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-cyanochroman-4-carboxylate

Product 1

HCID 462211084-(6-Cyano-4-(methoxycarbonyl)-chroman-7-yloxy)benzoic acidYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-cyanochroman-4-carboxylate (350 mg, 0.855 mmol) was diluted with dichloromethane (2 mL) and treated with TFA (2 mL). After stirring for 3 hours, the reaction was concentrated. The crude material was purified using a biotage 40M cartridge eluting with 0.5% methanol/dichloromethane to 10% methanol/dichloromethane to yield 4-(6-cyano-4-(methoxycarbonyl)chroman-7-yloxy)benzoic acid (280 mg, 92.7% yield).

Workup

  1. concentrationthe reaction was concentrated
  2. customThe crude material was purified
  3. washeluting with 0.5% methanol/dichloromethane to 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-d13e0bc837cb4cd68cbf4bdfe185a208
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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