Trifluoroacetic acid → HCID 131732767, compound

HRID 1474431Notes

Reaction equation

HRID 1474431 reaction equation
C(OC([N:8]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([C:23]#[N:24])=[CH:18][C:17]=1[NH:25][C:26]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:27])C(=O)OC(C)(C)C)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:8][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([C:23]#[N:24])=[CH:18][C:17]=1[NH:25][C:26](=[O:27])[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 117949651HCID 117949651, compound

Product 1

HCID 131732767HCID 131732767, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butyl t-butoxycarbonyl(4-cyano-2-(((heptyloxy)carbonyl)amino)-6-methylphenyl)carbamate (416 mg, 0.85 mmol) obtained in Step 3 was dissolved in CH2Cl2 (3.0 mL), added with TFA (1.95 mL, 30 eq, 25.5 mmol) and stirred at room temperature for 2 hours. Subsequently, the mixture thus obtained was added with sat. NaHCO3 and extracted with CH2Cl2. The organic layer thus obtained was dried over MgSO4 and concentrated under reduced pressure to obtain the title compound in a white solid (245 mg, yield: 99%).

Workup

  1. customSubsequently, the mixture thus obtained
  2. extractionextracted with CH2Cl2
  3. customThe organic layer thus obtained
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-66805e8a885b4257bf0f8b3afb674318
Source dataset
uspto-grants-2015_04
Patent number
US09018233B2

Reaction notes

Loading…