Trifluoroacetic acid → HCID 67223049, compound

HRID 1968903Notes

Reaction equation

HRID 1968903 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:24][CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N:25]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[S:26]([C:29]3[CH:33]=[CH:32][N:31]([CH3:34])[N:30]=3)(=[O:28])=[O:27])[CH:21]=2)[CH2:16]1)=O)(C)(C)C>ClCCl>[CH2:35]([N:25]([C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[CH2:16][NH:15][CH2:24][CH2:23]2)[S:26]([C:29]1[CH:33]=[CH:32][N:31]([CH3:34])[N:30]=1)(=[O:28])=[O:27])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67222737HCID 67222737, compound

Product 1

HCID 67223049HCID 67223049, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 ml) was added to a cooled stirred solution of 6-[Benzyl-(1-methyl-1H-pyrazole-3-sulfonyl)-amino]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (391 mg, 0.80 mmol) in dichloromethane (20 ml). The mixture was allowed to warm to room temperature and stirred for 3 hrs then cooled and quenched with 2M NaOH until slightly basic. After diluting the reaction mixture with dichloromethane (100 ml) the organic phase was partitioned, dried over sodium sulfate and concentrated in vacuo to afford the title compound as a white solid (304 mg, 80% yield). HPLC retention time 2.97 min. Mass spectrum (ES+) m/z 383 (M+H).

Workup

  1. temperaturethen cooled
  2. customquenched with 2M NaOH until slightly basic
  3. additionAfter diluting the reaction mixture with dichloromethane (100 ml) the organic phase
  4. customwas partitioned
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e036177564594e95a9ae3f00dea19eff
Source dataset
uspto-grants-2013_04
Patent number
US08426442B2

Reaction notes

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