Trifluoroacetic acid → HCID 42640886, compound

HRID 707568Notes

Reaction equation

HRID 707568 reaction equation
[C:1]([C:3]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=2[S:17]([CH3:20])(=[O:19])=[O:18])[N:7]([CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])[C:6](=[O:29])[N:5]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=2)[C:4]=1[CH3:40])#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1[C@@H:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=2[S:17]([CH3:20])(=[O:19])=[O:18])[N:7]([CH2:21][C:22]([OH:24])=[O:23])[C:6](=[O:29])[N:5]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:37])([F:39])[F:38])[CH:31]=2)[C:4]=1[CH3:40])#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86650722HCID 86650722, compound

Product 1

HCID 42640886HCID 42640886, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction was carried out under argon. tert-Butyl [(6R)-5-cyano-6-[4-cyano-2-(methylsulfonyl)phenyl]-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidin-1(2H)-yl]acetate (350 mg, 609 μmol; Example 7) was initially charged in dichloromethane (60 ml), and trifluoroacetic acid (20 ml) was added. The mixture was stirred at RT for 90 min. The volatile components were then removed on a rotary evaporator. The residue was taken up in toluene (50 ml) and again concentrated under reduced pressure. This procedure was repeated once more. The crude product was purified by preparative HPLC (column: Gromsil C-18 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). The title compound was obtained as a colorless solid (290 mg, 92% of theory).

Workup

  1. customThe volatile components were then removed on a rotary evaporator
  2. concentrationagain concentrated under reduced pressure
  3. customThe crude product was purified by preparative HPLC (column: Gromsil C-18 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10)

Sources & evidence

ORD record
ord-37be25e04e924107bc7eef86f6347573
Source dataset
uspto-grants-2015_11
Patent number
US09174997B2

Reaction notes

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