Trifluoroacetic acid → 2-[(1,2,3,4-Tetrahydro-isoquinoline-5-carbonyl)-amino]-indan-2-carboxylic acid

HRID 1047728Notes

Reaction equation

HRID 1047728 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[C:18](=[O:32])[NH:19][C:20]2([C:29]([OH:31])=[O:30])[CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21]2)[CH2:9]1)=O)(C)(C)C.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34].[CH2:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([C:18]([NH:19][C:20]3([C:29]([OH:31])=[O:30])[CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21]3)=[O:32])[C:15]=2[CH2:16][CH2:17][NH:8]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593143385-(2-Carboxy-indan-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 2

HCID 6422Trifluoroacetic acidHCID 593142982-[(1,2,3,4-Tetrahydro-isoquinoline-5-carbonyl)-amino]-indan-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(2-Carboxy-indan-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (72) (650 mg, 1.49 mmol) is dissolved in 30% solution of TFA in DCM (10 mL) and the resulting solution is stirred at RT for 2 h. The solution is concentrated to give a TFA salt of 2-[(1,2,3,4-tetrahydro-isoquinoline-5-carbonyl)-amino]-indan-2-carboxylic acid (670 mg, 100%). This TFA salt (250 mg, 0.56 mmol) is dissolved in 6N aqueous solution of HCl (20 mL). The resulting suspension is stirred overnight and turned into a clear solution. The solution is concentrated to give a pure product (73) as white solid (130 mg, 62%).

Workup

  1. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-950f3fb7d2df429dbc15141465660b94
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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