Trifluoroacetic acid → (3R)-3-{3-[(2-amino-2-oxoethoxy)methyl]-1,2,4-oxadiazol-5-yl}6-cyclohexylhexanoic acid

HRID 1279875노트

반응식

HRID 1279875 반응식
[NH2:1][C:2](=[O:29])[CH2:3][O:4][CH2:5][C:6]1[N:10]=[C:9]([C@H:11]([CH2:20][CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[O:8][N:7]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:1][C:2](=[O:29])[CH2:3][O:4][CH2:5][C:6]1[N:10]=[C:9]([C@H:11]([CH2:20][CH2:21][CH2:22][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:12][C:13]([OH:15])=[O:14])[O:8][N:7]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 59909799tert-Butyl (3R)-3-{3-[(2-amino-2-oxoethoxy)methyl]-1,2,4-oxadiazol-5-yl}-6-cyclohexylhexanoate

생성물 1

HCID 59909790(3R)-3-{3-[(2-amino-2-oxoethoxy)methyl]-1,2,4-oxadiazol-5-yl}6-cyclohexylhexanoic acid수율 51%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of tert-butyl (3R)-3-{3-[(2-amino-2-oxoethoxy)methyl]-1,2,4-oxadiazol-5-yl}-6-cyclohexylhexanoate (Preparation 90) (280 mg, 0.86 mmol) in dichloromethane (7 ml) was treated with trifluoroacetic acid (3 ml) and stirred at room temperature for 4 hours. The solvent was removed under reduced pressure and the residue azeotroped from toluene and dichloromethane. The oil was purified by column chromatography on silica gel eluting with a gradient system of 100:0:0 (dichloromethane:methanol:acetic acid) gradually changing to 90:10:1 (dichloromethane:methanol:acetic acid) to afford a colourless oil which was triturated with diethyl ether and filtered to afford the title compound (155 mg).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped from toluene and dichloromethane
  3. customThe oil was purified by column chromatography on silica gel eluting with a gradient system of 100:0:0 (dichloromethane:methanol:acetic acid)
  4. customto afford a colourless oil which
  5. customwas triturated with diethyl ether
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-55c58c9f629245b985873d589b523662
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06448278B2

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