Trifluoroacetic acid → HCID 57635427, compound

HRID 535977Notes

Reaction equation

HRID 535977 reaction equation
[F:1][C:2]([CH3:35])([CH3:34])[CH:3]([NH:8][C:9]([C:11]1[N:12]=[C:13]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:14]2[CH2:20][CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][C:15]=12)=[O:10])[C:4]([NH:6][CH3:7])=[O:5].FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]([CH3:35])([CH3:34])[CH:3]([NH:8][C:9]([C:11]1[N:12]=[C:13]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:14]2[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][C:15]=12)=[O:10])[C:4]([NH:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57635485HCID 57635485, compound

Product 1

HCID 57635427HCID 57635427, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 66D (178 mg, 0.37 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (1.12 mL, 14.60 mmol). After 1 hour of stirring, the solution was concentrated under reduced pressure. The residue was brought to pH 8 with a saturated aqueous solution of sodium bicarbonate. The aqueous solution was extracted with dichloromethane. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to yield Compound 604 as a white solid (117 mg, 83%). 1H-NMR (400 MHz, (CD3)2SO) δ: 1.31 (d, 3H), 1.37 (d, 3H), 1.71 (m, 2H), 2.61 (d, 3H), 3.00 (m, 2H), 4.13 (m, 2H), 4.28 (m, 2H), 4.64 (dd, 1H), 7.52 (m, 5H), 7.81 (d, 1H), 8.24 (q, 1H). LCMS (+ESI) m/z 388.1 [M+H]+.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. extractionThe aqueous solution was extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-112e68d9fdaa41e4b3f0eb283159c9df
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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