Hydrochloric Acid → HCID 178450804, 화합물

HRID 2169379노트

반응식

HRID 2169379 반응식
[C:1]1([C:11]2([CH2:16][C:17]([NH2:19])=[NH:18])[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[C:21]([O:25][C:26](=[O:41])/[C:27](/O)=[C:28](\[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)/[C:29](O)=[O:30])([CH3:24])([CH3:23])[CH3:22].C[O-].[Na+]>CO.CCCCCC.C(OCC)(=O)C>[C:21]([O:25][C:26]([C:27]1[C:28]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:29]([OH:30])[N:19]=[C:17]([CH2:16][C:11]2([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[CH2:15][CH2:14][CH2:13][CH2:12]2)[N:18]=1)=[O:41])([CH3:24])([CH3:22])[CH3:23]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86725882(E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl esterHCID 867260082-(1-Naphthalen-1-yl-cyclopentyl)-acetamidine

생성물 1

HCID 178450804HCID 178450804, 화합물수율 48%

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-naphthalen-1-yl-cyclopentyl)-acetamidine; hydrochloride (343) (4.5 g, crude) in methanol (30 mL) were added (E,Z)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester (4) (5.759 g, 18.7 mmol) and the reaction mixture was cooled to 0° C. in a ice bath. To this reaction mixture was then added sodium methoxide (25% in methanol, 10.1 mL, 46.74 mmol) and the reaction mixture was stirred at room temperature for 18 h (silica TLC, 50% ethyl acetate in hexane; Rf=0.5). The reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (50 mL) and brine (50 mL). The organic phase was thereafter dried and concentrated under vacuum to get a crude mass which was purified by CombiFlash eluted with a gradient mixture of ethyl acetate and hexane to get pure 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (344) (4.1 g, 48%, 2 steps) as a brown sticky mass.

후처리

  1. washwashed with water (50 mL) and brine (50 mL)
  2. customThe organic phase was thereafter dried
  3. concentrationconcentrated under vacuum
  4. customto get a crude mass which
  5. customwas purified by CombiFlash
  6. washeluted with a gradient mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-1efd90963abd4813a6530a7d52b62aeb
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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