Trifluoroacetic acid → HCID 87285518, compound

HRID 574270Notes

Reaction equation

HRID 574270 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[CH2:9][N:10]1[C:15](=[O:16])[C:14]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[O:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=3)[CH:19]([CH2:33][OH:34])[CH2:18]2)=[C:13]([CH3:35])[N:12]([CH2:36][C:37]2[C:42]([C:43]([F:46])([F:45])[F:44])=[CH:41][CH:40]=[CH:39][C:38]=2[F:47])[C:11]1=[O:48])(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:7][C@H:8]([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[CH2:9][N:10]1[C:15](=[O:16])[C:14]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[O:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=3)[CH:19]([CH2:33][OH:34])[CH2:18]2)=[C:13]([CH3:35])[N:12]([CH2:36][C:37]2[C:42]([C:43]([F:45])([F:46])[F:44])=[CH:41][CH:40]=[CH:39][C:38]=2[F:47])[C:11]1=[O:48]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 87285698HCID 87285698, compound

Product 1

HCID 87285518HCID 87285518, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((R)-2-{3-(2-fluoro-6-trifluoromethyl-benzyl)-5-[3-hydroxymethyl-4-(5-trifluoromethyl-furan-2-ylmethyl)-piperazin-1-yl]-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl}-1-phenyl-ethyl)-carbamic acid tert-butyl ester (17 mg, 0.022 mmol) in dichloromethane (1 mL) was added trifluoroacetic acid (100 μl, 1.30 mmol), followed by at room temperature for 1 hr. The solution was neutralized with an aqueous saturated sodium bicarbonate solution. After concentration of the organic layer thus formed, the residue was purified using silica gel chromatography (eluent: dichloromethane/methanol, 10/1) and dried in a vacuum to afford 12 mg of the compound as a white foam (yield 81%). 1H NMR (300 MHz, CDCl3) δ 2.29 (3H, s), 2.50 (3H, m), 2.86 (2H, m), 3.50-3.76 (3H, m), 3.95 (2H, m), 4.04 (2H, m), 4.21 (1H, t), 4.36 (1H, dd), 5.40 (2H, dd), 6.30 (1H, s), 6.73 (1H, s), 7.22 (2H, m), 7.33 (2H, t), 7.40 (3H, m), 7.54 (1H, d) MS (ESI) m/z 684.4 (MH+)

Workup

  1. customAfter concentration of the organic layer thus formed
  2. customthe residue was purified
  3. customdried in a vacuum

Sources & evidence

ORD record
ord-601e51ec0f434a0eb9dc3147820f2a7b
Source dataset
uspto-grants-2015_05
Patent number
US09034850B2

Reaction notes

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