Trifluoroacetic acid → HCID 67414871, compound

HRID 716110Notes

Reaction equation

HRID 716110 reaction equation
C(OC(=O)[NH:7][CH:8]([CH:63]1[CH2:68][CH2:67][CH2:66][CH2:65][CH2:64]1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([CH2:26][CH2:27][O:28][CH2:29][CH2:30][N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]([CH2:40][CH:41]3[CH2:45][CH2:44][CH2:43][N:42]3[C:46](=[O:62])[CH:47]([NH:54]C(OC(C)(C)C)=O)[CH:48]3[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]3)=[CH:32]2)[CH:18]=1)=[O:10])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][CH:8]([CH:63]1[CH2:68][CH2:67][CH2:66][CH2:65][CH2:64]1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([CH2:26][CH2:27][O:28][CH2:29][CH2:30][N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]([CH2:40][CH:41]3[CH2:45][CH2:44][CH2:43][N:42]3[C:46](=[O:62])[CH:47]([NH2:54])[CH:48]3[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]3)=[CH:32]2)[CH:18]=1)=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 76571757HCID 76571757, compound

Product 1

HCID 67414871HCID 67414871, compoundYield 113.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing 48 (0.085 g, 0.08 mmol) in DCM (8 mL) was cooled to 0° C. Trifluoroacetic acid (2 mL) was added and the reaction mixture was maintained at 0° C. for 30 min. An additional portion of TFA (1 mL) was added and the reaction mixture was stirred for 1 h at 0° C. The reaction was quenched by the careful addition of saturated aqueous NaHCO3 and the product was extracted with EtOAc. The combined organic extracts were washed with aq. NaHCO3, brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 0.068 g of 49 as a pale yellow oil. The crude product was used directly in the next reaction. 1H NMR (CDCl3, 300 MHz) δ7.90 (d, J=7.6 Hz, 2H), 7.31-7.12 (m, 6H), 6.84 (app t, J=14 Hz, 2H), 4.47 (m, minor rotomer), 4.15 (m, 4H), 3.66-3.36 (m, 8H), 2.80 (m, 2H), 2.42 (m, 2H), 2.04-0.83 (m, 30H) ppm.

Workup

  1. temperaturethe reaction mixture was maintained at 0° C. for 30 min
  2. customThe reaction was quenched by the careful addition of saturated aqueous NaHCO3
  3. extractionthe product was extracted with EtOAc
  4. washThe combined organic extracts were washed with aq. NaHCO3, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e1143c6b52424e5baa3e6f0f1ce900d3
Source dataset
uspto-grants-2015_11
Patent number
US09187490B2

Reaction notes

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