Dichloroacetic Acid → HCID 11796530, 화합물

HRID 2293800노트

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HRID 2293800 반응식
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]

참가 물질

7

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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

생성물 1

HCID 11796530HCID 11796530, 화합물수율 66.2%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 1140Toluene용매

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온도
20 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a11ba18d00f34228b5b3ba7761eb16d8
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05686628

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