Hydrochloric Acid → HCID 178450804、化合物

HRID 2169379ノート

反応式

HRID 2169379 の反応式
[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]

参加物

8

反応物 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

生成物 1

HCID 178450804HCID 178450804、化合物収率 48%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1efd90963abd4813a6530a7d52b62aeb
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

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