Trifluoromethanesulfonic acid → HCID 19695845, compound

HRID 863421Notes

Reaction equation

HRID 863421 reaction equation
C(OC([NH:11][C:12]1[C:13](=[O:48])[N:14]([CH2:24][C:25]([NH:27][CH:28]([CH:45]([CH3:47])[CH3:46])[C:29](=[O:44])[C:30]([F:43])([F:42])[C:31](=[O:41])[NH:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:26])[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][CH:17]=1)=O)C1C=CC=CC=1.FC(F)(F)S(O)(=O)=O>ClCCl.C1(OC)C=CC=CC=1>[NH2:11][C:12]1[C:13](=[O:48])[N:14]([CH2:24][C:25]([NH:27][CH:28]([CH:45]([CH3:46])[CH3:47])[C:29](=[O:44])[C:30]([F:43])([F:42])[C:31](=[O:41])[NH:32][CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:26])[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 19695810HCID 19695810, compound

Product 1

HCID 19695845HCID 19695845, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of 2-(3-benzyloxycarbonylamino-2-oxo-6-phenyl-1,2-dihydro-1-pyridyl)-N-[3,3-difluoro-1-isopropyl-2-oxo-3-(N-phenethylcarbamoyl)propyl]acetamide (0.451 g) in dichloromethane (7 mL) and anisole (0.22 mL) was added trifluoromethanesulfonic acid (0.30 mL). After 1.5 h, the reaction was quenched with saturated sodium bicarbonate. The mixture was extracted with dichloromethane, and the extracts were washed (saturated sodium bicarbonate, brine), dried, and evaporated. The crude product was purified by chromatography, twice, with dichloromethane:methanol (first column: gradient, 99:1, 92:8; second column: gradient, 99:1, 92:8) as the eluent. The resulting material was crystallized from ether and petroleum ether to give the title compound (0.119 g) as a tan solid; TLC: Rf =0.27, dichloromethane:methanol (98:2); 300 MHz NMR: 9.20 (t,1), 8.42 (d,1), 7.38-7.18 (m,10), 6.51 (d,1), 5.97 (d,1), 5.15 (d,2), 4.80 (dd,1), 4.43 (broad s,2), 3.43-3.29 (m,2), 2.76 (t,2), 2.29-2.13 (m,1), 0.85 (d,3), 0.74 (d,3); MS: m/z=525(M+1).

Workup

  1. customthe reaction was quenched with saturated sodium bicarbonate
  2. extractionThe mixture was extracted with dichloromethane
  3. washthe extracts were washed (saturated sodium bicarbonate, brine)
  4. customdried
  5. customevaporated
  6. customThe crude product was purified by chromatography
  7. customThe resulting material was crystallized from ether and petroleum ether

Sources & evidence

ORD record
ord-77319f1997564fb9b0204cede97c1514
Source dataset
uspto-grants-1998_02
Patent number
US05721222

Reaction notes

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