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Trifluoromethanesulfonic acid, lithium salt → (R)-3-(7-Fluoro-2-oxo-1-propyl-2,3-dihydro-1H-indol-5-ylamino)-2-hydroxy-propionic acid methyl ester

HRID 2114893
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HRID 2114893 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH2:12][CH2:13][CH3:14])[C:6](=[O:15])[CH2:5]2.[CH3:16][O:17][C:18]([C@@H:20]1[O:22][CH2:21]1)=[O:19].FC(F)(F)S([O-])(=O)=O.[Li+]>C(#N)C.C(OCC)(=O)C>[CH3:16][O:17][C:18](=[O:19])[C@H:20]([OH:22])[CH2:21][NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH2:12][CH2:13][CH3:14])[C:6](=[O:15])[CH2:5]2
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참가 물질

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반응물 3

HCID 3664839Trifluoromethanesulfonic acid, lithium saltHCID 9877347Methyl (2R)-2-oxiranecarboxylateHCID 692741315-Amino-7-fluoro-1-propyl-1,3-dihydro-indol-2-one

생성물 1

HCID 69274128(R)-3-(7-Fluoro-2-oxo-1-propyl-2,3-dihydro-1H-indol-5-ylamino)-2-hydroxy-propionic acid methyl ester

시약·촉매·용매 2

HCID 6342Acetonitrile용매
HCID 8857
Ethyl Acetate
용매

실험 절차

5-Amino-7-fluoro-1-propyl-1,3-dihydro-indol-2-one (0.300 g, 1.44 mmol), methyl (2R)-glycidate (0.147 g, 1.44 mmol) and lithium trifluoromethanesulfonate (0.220 g, 1.44 mmol) in acetonitrile (5 ml) are heated at 90° C. for 8 hours. The reaction is diluted with ethyl acetate, washed with water and brine, dried (Na2SO4) and evaporated. The residue is purified by PTLC (5% methanol/dichloromethane) to give the title compound as a yellow solid. HPLC r.t. 4.03 min; MS for C15H19FN2O4 m/z 311.2 (M+H)+.

후처리

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue is purified by PTLC (5% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-9a2ed9b7546049059c0e7b844a3ceec7
출처 데이터셋
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07435751B2

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