Trifluoroacetic acid → HCID 86705888, compound

HRID 339250Notes

Reaction equation

HRID 339250 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7](C(OC(C)(C)C)=O)[CH:6]([C:19](=[O:31])[NH:20][C@H:21]1[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24][CH2:23][CH2:22]1)[CH2:5]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][NH:7][CH:6]([C:19]([NH:20][C@H:21]1[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24][CH2:23][CH2:22]1)=[O:31])[CH2:5]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86705889HCID 86705889, compound

Product 1

HCID 86705888HCID 86705888, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 6-hydroxy-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (875 mg, 2.07 mmol) in CH2Cl2 (10.4 mL) was added TFA (2.4 mL, 31.1 mmol). The resulting solution was stirred at room temperature for 2 h and then quenched with sat. NaHCO3. The aqueous layer was extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (340 mg, 51%) as pale yellow solid. MS (ESI+) m/z 323.2 (M+H)+.

Workup

  1. customquenched with sat. NaHCO3
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c528cf7e388d480b88ec815e145f17eb
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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