Dichloroacetic Acid → HCID 11796530、化合物

HRID 2393803ノート

反応式

HRID 2393803 の反応式
Cl.CN(C)CCCN=C=NCC.[CH3:13][O:14][C:15]([NH:17][C@@H:18]([CH:39]([CH3:41])[CH3:40])[C:19]([N:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[C:26]([NH:28][CH:29]([CH:33]([OH:38])[C:34]([F:37])([F:36])[F:35])[CH:30]([CH3:32])[CH3:31])=[O:27])=[O:20])=[O:16].ClC(Cl)C(O)=O.C(OCC)(=O)C>CS(C)=O.C1(C)C=CC=CC=1>[CH3:13][O:14][C:15]([NH:17][C@@H:18]([CH:39]([CH3:41])[CH3:40])[C:19]([N:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[C:26]([NH:28][CH:29]([C:33](=[O:38])[C:34]([F:37])([F:36])[F:35])[CH:30]([CH3:32])[CH3:31])=[O:27])=[O:20])=[O:16]

参加物

7

反応物 4

HCID 6597Dichloroacetic AcidHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10693669(S)-1-[(S)-2-(methoxycarbonylamino)-3-methylbutyryl]-N-[2-methyl-1-(2,2,2-trifluoro-1-hydroxyethyl)propyl]-pyrrolidine-2-carboxamide

生成物 1

HCID 11796530HCID 11796530、化合物収率 66.2%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 1140Toluene溶媒

反応条件

温度
20 °C

実験手順

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.84 g) was added to a solution of (S)-1-[(S)-2-(methoxycarbonylamino)-3-methylbutyryl]-N-[2-methyl-1-(2,2,2-trifluoro-1-hydroxyethyl)propyl]pyrrolidine-2-carboxamide (0.41 g) dissolved in dimethylsulphoxide (DMSO; 5 ml) and toluene (5 ml), followed by dropwise addition of dichloroacetic acid (0.32 ml). The resulting solution was allowed to stir at 20° C. for 2 hours. The solution was then poured into ethyl acetate (200 ml) and washed successively with 1M hydrochloric acid, water and brine. The organic solution was dried (MgSO4) and concentrated under vacuum. The residue was purified by flash chromatography (gradient elution; methanol:methylene chloride, 3:97 to 5:95) to give (S)-1-[(S)-2-(methoxycarbonylamino)-3-methylbutyryl]-N-[2-methyl-1-(2,2,2-trifluoroacetyl)propyl]pyrrolidine-2-carboxamide (0.27 g) as a white foam (as a mixture of ketone and hydrated forms); TLC, Rf =0.4 (methanol:dichloromethane, 2.5:97.5); 1H NMR (DMSO/D2O): 4.44 (m, 1H), 4.00 (m, 2H), 3.72 (m, 1H), 3.51 (m, 4H), 202-1.75 (m, 6H), 0.95-0.78 (m, 12H); Analysis for C18H28F3N3O5 0.3H2O: Calculated: C, 50.42; H, 6.72; N, 9.80; Found: C, 50.31; H, 6.28; N, 9.56.

後処理

  1. washwashed successively with 1M hydrochloric acid, water and brine
  2. dry with materialThe organic solution was dried (MgSO4)
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by flash chromatography (gradient elution; methanol:methylene chloride, 3:97 to 5:95)

出典と根拠

ORDレコード
ord-ee7fde0efb004805a3e99d4e136fcdd1
出典データセット
uspto-grants-1998_09
特許番号
US05808097

反応ノート

読み込み中…