Triethylamine → {4-[2-Oxo-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-cyclohexylmethyl}-carbamic acid benzyl ester

HRID 1796999ノート

反応式

HRID 1796999 の反応式
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)=[O:5].[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH:31]([C:34](O)=[O:35])[CH2:30][CH2:29]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.O>[CH2:16]([O:23][C:24](=[O:25])[NH:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH:31]([C:34](=[O:35])[NH:2][CH2:3][C:4](=[O:5])[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:13])([F:14])[F:15])[CH:7]=2)[CH2:30][CH2:29]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 3723035Cbz-trans-4-(aminomethyl)cyclohexanecarboxylic acidHCID 133658852-Amino-1-(3-(trifluoromethyl)phenyl)ethan-1-one hydrochloride

生成物 1

HCID 12154029{4-[2-Oxo-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-cyclohexylmethyl}-carbamic acid benzyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-Amino-1-(3-trifluoromethyl-phenyl)-ethanone hydrochloride (3.4 g, 0.0144 mol (prepared according to the procedure of Leclerc and Bizec (1980) J. Med. Chem. 23:783–744) and 4-(Benzyloxycarbonylamino-methyl)-cyclohexanecarboxylic acid (4.2 g, 0.0144 mol; for a preparation of this reagent see e.g., Svahn et. al. (1986) J. Med. Chem. 29:448–453) in DMF, Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent, 6.4 g, 0.0144 mol) was added, followed by triethylamine (4.0 mL, 0.0289 mol). The reaction was stirred overnight and then poured into water to produce a thick precipitate. The solid was collected on a sintered glass funnel and washed consecutively with H2O, 3N HCl (2×), H2O, NaHCO3 solution (2×) and H2O. The filter cake was air dried, added to a 500 mL round bottom flask with toluene and concentrated under reduced pressure. Additional toluene (200 mL) was added and the mixture was concentrated again under reduced pressure to yield {4-[2-Oxo-2-(3-trifluoromethyl-phenyl)-ethylcarbamoyl]-cyclohexylmethyl}-carbamic acid benzyl ester as a solid. 1H NMR (DMSO-d6): δ0.8–0.93 (m, 2H), 1.2–1.37 (m, 3H), 1.71 (br s, 4H), 2.14 (t, 1H), 2.84 (br s, 2H), 4.57 (br s, 2H), 4.99 (s, 2H), 7.2–7.38 (m, 5H), 7.77(t, 1H), 8.01 (d, J=8.0 Hz, 1H), 8.14–8.26 (m, 3H). MS 477 (M+H)+

後処理

  1. customfor a preparation of this reagent
  2. customto produce a thick precipitate
  3. customThe solid was collected on a sintered glass funnel
  4. washwashed consecutively with H2O, 3N HCl (2×), H2O, NaHCO3 solution (2×) and H2O
  5. customdried
  6. additionadded to a 500 mL round bottom flask with toluene
  7. concentrationconcentrated under reduced pressure
  8. additionAdditional toluene (200 mL) was added
  9. concentrationthe mixture was concentrated again under reduced pressure

出典と根拠

ORDレコード
ord-9158216d6c9c49c480054346d4bb746c
出典データセット
uspto-grants-2006_04
特許番号
US07034034B2

反応ノート

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