Potassium Carbonate → {2-[3-(2-Fluoro-3-methoxy-phenyl)-5-(2-fluoro-6-trifluoromethyl-benzyl)-2,4,6-trioxo-[1,3,5]triazinan-1-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester

HRID 1838929ノート

反応式

HRID 1838929 の反応式
[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]([CH3:29])([CH3:28])[CH2:9][N:10]1[C:15](=[O:16])[NH:14][C:13](=[O:17])[N:12]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:19]=2[F:26])[C:11]1=[O:27])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[F:37][C:38]1[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:48])[F:47])[C:39]=1[CH2:40]Br>CN(C=O)C>[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]([CH3:29])([CH3:28])[CH2:9][N:10]1[C:15](=[O:16])[N:14]([CH2:40][C:39]2[C:42]([C:46]([F:47])([F:49])[F:48])=[CH:43][CH:44]=[CH:45][C:38]=2[F:37])[C:13](=[O:17])[N:12]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:19]=2[F:26])[C:11]1=[O:27])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27375732-(Bromomethyl)-1-fluoro-3-(trifluoromethyl)benzeneHCID 69556374{2-[3-(2-Fluoro-3-methoxy-phenyl)-2,4,6-trioxo-[1,3,5]triazinan-1-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester

生成物 1

HCID 69892014{2-[3-(2-Fluoro-3-methoxy-phenyl)-5-(2-fluoro-6-trifluoromethyl-benzyl)-2,4,6-trioxo-[1,3,5]triazinan-1-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

{2-[3-(2-Fluoro-3-methoxy-phenyl)-2,4,6-trioxo-[1,3,5]triazinan-1-yl]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (370 mg) was dissolved in 7 mL of anhydrous DMF. To this solution was added K2CO3 (2.0 eq, 226 mg) and 2-fluoro-6-(trifluoromethyl)benzyl bromide (1.0 eq, 222 mg). The reaction was complete by LC/MS after 14 hours. The DMF was removed in vacuo. The residue was partitioned between EtOAc and H2O. The EtOAc layer was collected and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via flash column chromatography and eluted with 30% EtOAc/hexanes to yield 399 mg (76%). Rf=0.36 in 30% EtOAc/hexanes. 1H NMR (CDCl3) δ: 7.51 (d,1H), 7.39 (m,1H), 7.27 (d,1H), 7.15 (dt,1H), 7.06 (dt,1H), 6.88 (dt,1H), 5.42 (q,2H), 5.15 (bs,1H), 4.14 (q,2H), 3.9 (s,3H), 1.4 (s,9H), 1.39 (d,6H).

後処理

  1. customThe DMF was removed in vacuo
  2. customThe residue was partitioned between EtOAc and H2O
  3. customThe EtOAc layer was collected
  4. extractionthe aqueous layer was extracted with EtOAc (2×20 mL)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified via flash column chromatography
  10. washeluted with 30% EtOAc/hexanes
  11. customto yield 399 mg (76%)

出典と根拠

ORDレコード
ord-08257733f351436fa09eeaed81efc665
出典データセット
uspto-grants-2004_01
特許番号
US06677340B2

反応ノート

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