Trifluoroacetic acid → HCID 57635427, compound

HRID 1971129Notes

Reaction equation

HRID 1971129 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-585e8d3402d742bf89407e8ed25a8e13
Source dataset
uspto-grants-2013_04
Patent number
US08431565B2

Reaction notes

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