Sodium Methoxide → HCID 178450811, 화합물

HRID 2169359노트

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HRID 2169359 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13][C:14]([NH2:16])=[NH:15])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.C1(C2(CC(N)=N)CCCC2)C=CC=CC=1.[C:33]([O:37][C:38](=[O:53])/[C:39](/O)=[C:40](\[O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)/[C:41](O)=[O:42])([CH3:36])([CH3:35])[CH3:34].C[O-].[Na+]>CO.C(OCC)(=O)C.CCCCCC>[C:33]([O:37][C:38]([C:39]1[C:40]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[C:41]([OH:42])[N:16]=[C:14]([CH2:13][C:8]2([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:15]=1)=[O:53])([CH3:36])([CH3:34])[CH3:35]

참가 물질

8

반응물 4

HCID 10942334Sodium MethoxideHCID 867258072-(1-Phenyl-cyclopentyl)-acetamidine HCl saltHCID 867258102-[1-(4-Chlorophenyl)-cyclopentyl]-acetamidineHCID 86725882(E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester

생성물 1

HCID 178450811HCID 178450811, 화합물수율 91%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매2회

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온도
0 °C

실험 절차

To a stirred solution of 2-[1-(4-chlorophenyl)-cyclopentyl]-acetamidine; hydrochloride (322) (3.1 g, 11.34 mmol) in methanol (25 mL) was added (E,Z)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester (4) (4.19 g, 13.61 mmol) and cooled to 0° C. To this reaction mixture was then added sodium methoxide (25% in methanol) (7.4 mL, 34.03 mmol) and stirred at room temperature for 16 h (TLC; ethyl acetate:hexane=1:1, Rf=0.5). The reaction mixture was diluted with ethyl acetate (300 mL), washed with water (60 mL) and brine (60 mL) and dried and concentrated in vacuo to get crude mass which was purified by CombiFlash eluted with gradient polarity mobile phase (hexane to 50% ethyl acetate in hexane) to get pure 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (323) (5.1 g, 91%) as a light brown solid.

후처리

  1. washwashed with water (60 mL) and brine (60 mL)
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customto get crude mass which
  5. customwas purified by CombiFlash
  6. washeluted with gradient polarity mobile phase (hexane to 50% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-484d261894284809ab340e823713ac9f
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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