Trifluoroacetic acid → 2-Amino-3-[(3R,4S)-3-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}oxy)-4-phenylpyrrolidin-1-yl]-3-oxopropan-1-ol

HRID 2377037ノート

反応式

HRID 2377037 の反応式
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@@H:16]2[C@@H:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:19][N:18]([C:27]([CH:29]3[CH2:33][O:32]C(C)(C)[N:30]3C(OC(C)(C)C)=O)=[O:28])[CH2:17]2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:30][CH:29]([C:27]([N:18]1[CH2:19][C@H:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@@H:16]([O:15][C@@H:13]([C:5]2[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([C:2]([F:44])([F:1])[F:43])[CH:4]=2)[CH3:14])[CH2:17]1)=[O:28])[CH2:33][OH:32]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 11433611tert-Butyl 4-{[(3R,4S)-3-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}oxy)-4-phenylpyrrolidin-1-yl]carbonyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

生成物 1

HCID 112717972-Amino-3-[(3R,4S)-3-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}oxy)-4-phenylpyrrolidin-1-yl]-3-oxopropan-1-ol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 48 mg tert-butyl 4-{[(3R,4S)-3-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}oxy)-4-phenylpyrrolidin-1-yl]carbonyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (Example 4) in 3 mL methylene chloride was added 0.5 mL anisole and 3 mL TFA. The reaction mixture was stirred at RT for 2 hr and then the volatiles were removed under vacuum. The residue was partitioned between methylene chloride (5 mL) and sat. aq. sodium carbonate (5 mL). The organic layer was dried over sodium sulfate, filtered and the solvent removed under vacuum. The residue was purified by prep TLC eluting with methylene chloride/methanol (9/1) to afford the title compound. 1H-NMR (CDCl3): δ: 1.43 (d, 3H, 6.5 Hz), 2.0 (br. s, 3H), 3.30-4.18 (m, 9H), 4.54 (m, 1H), 7.00-7.08 (m, 2H), 7.22-7.31 (m, 3H), 7.56 (s, 2H), 7.75 (s, 1H)ppm. MS: 491.2 (MH+) observed.

後処理

  1. customthe volatiles were removed under vacuum
  2. customThe residue was partitioned between methylene chloride (5 mL) and sat. aq. sodium carbonate (5 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under vacuum
  6. customThe residue was purified by prep TLC
  7. washeluting with methylene chloride/methanol (9/1)

出典と根拠

ORDレコード
ord-8d52966cafd049edb5f1ee3c5bebacf6
出典データセット
uspto-grants-2008_12
特許番号
US07468437B2

反応ノート

読み込み中…