Hydrochloric Acid → (5-{2-[(3',4',5'-Trimethoxy-biphenyl-2-carbonyl)-amino]-phenyl}-thiophen-2-yl)-acetic acid

HRID 2075939Notes

Reaction equation

HRID 2075939 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][C:5]1[S:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17]([C:19]2[C:20]([C:25]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=3)=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:18])=[CH:8][CH:9]=1.[Li+].[OH-].Cl>CC#N>[CH3:32][O:31][C:29]1[CH:30]=[C:25]([C:20]2[C:19]([C:17]([NH:16][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:7]3[S:6][C:5]([CH2:4][C:3]([OH:37])=[O:2])=[CH:9][CH:8]=3)=[O:18])=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[C:27]([O:35][CH3:36])[C:28]=1[O:33][CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59785699(5-{2-[(3',4',5'-Trimethoxy-biphenyl-2-carbonyl)-amino]-phenyl}-thiophen-2-yl)-acetic acid methyl ester

Product 1

HCID 59785707(5-{2-[(3',4',5'-Trimethoxy-biphenyl-2-carbonyl)-amino]-phenyl}-thiophen-2-yl)-acetic acidYield 99.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dissolve (5-{2-[(3′,4′,5′-Trimethoxy-biphenyl-2-carbonyl)-amino]-phenyl}-thiophen-2-yl)-acetic acid methyl ester (58) (56 mg, 0.11 mmol) in MeCN (3.8 mL) at rt and add 1M aqu LiOH (760 μL, 0.76 mmol). Stir reaction mixture 18 h at rt. Quench reaction mixture (cooling bath) with 2M aqu. HCl. Extract the mixture with EtOAc (3×), wash the combined organic layer with brine and dry with Na2SO4 to obtain (5-{2-[(3′,4′,5′-Trimethoxy-biphenyl-2-carbonyl)-amino]-phenyl}-thiophen-2-yl)-acetic acid (59) (55 mg, 99%) as a brown solid. 1H NMR (400 MHz, CDCl3): 3.76 (s, 6H), 3.80 (s, 3H); 3.83 (s, 2H); 6.32 (d, 1H, J=3.5 Hz); 6.60 (s, 2H); 6.78 (d, 1H, J=3.5 Hz); 7.07 (t, 1H, J=7.6 Hz); 7.23 (d, 1H, J=7.6 Hz); 7.32 (t, 1H, J=7.6 Hz); 7.36-7.54 (m, 3H); 7.69 (d, 1H, J=8.0 Hz); 8.43 (d, 1H, J=8.0 Hz).

Workup

  1. customreaction mixture 18 h at rt
  2. customQuench
  3. customreaction mixture (cooling bath) with 2M aqu
  4. extractionExtract the mixture with EtOAc (3×)
  5. washwash the combined organic layer with brine
  6. dry with materialdry with Na2SO4

Sources & evidence

ORD record
ord-d587724f2c774484963bb8ba01cf0961
Source dataset
uspto-grants-2011_04
Patent number
US07923473B2

Reaction notes

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