Cyclopentanol → [4-(5-Cyclopentyloxy-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester

HRID 403467ノート

反応式

HRID 403467 の反応式
[C:1]([O:5][C:6](=[O:34])[CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[O:17][C:18]3[N:19]=[C:20](S(C)(=O)=O)[N:21]=[C:22]([O:25][CH2:26][CH2:27][CH3:28])[C:23]=3[N:24]=2)=[CH:11][C:10]=1[CH3:33])([CH3:4])([CH3:3])[CH3:2].[CH:35]1([OH:40])[CH2:39][CH2:38][CH2:37][CH2:36]1.C(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)(C)C>>[C:1]([O:5][C:6](=[O:34])[CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[O:17][C:18]3[N:19]=[C:20]([O:40][CH:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[N:21]=[C:22]([O:25][CH2:26][CH2:27][CH3:28])[C:23]=3[N:24]=2)=[CH:11][C:10]=1[CH3:33])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 3

HCID 7298CyclopentanolHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneHCID 86679896Tert-butyl [4-(5-methanesulfonyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate

生成物 1

HCID 86679898[4-(5-Cyclopentyloxy-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester収率 27.2%

反応条件

温度
100 °C

実験手順

A solution of 98 mg of [4-(5-methanesulfonyl-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester, 19 mg of cyclopentanol and 69 mg of (tert-butylimino)tris(pyrrolidino)phosphorane was reacted at room temperature for 16 h and subsequently heated in a microwave reactor to 100° C. for 10 min. The mixture was poured onto water and extracted twice with ethyl acetate. The combined organic layers were washed with a 10% aqueous solution of citric acid and brine, dried and evaporated. After purification by preparative HPLC, 27 mg of the title compound were obtained.

後処理

  1. additionThe mixture was poured onto water
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with a 10% aqueous solution of citric acid and brine
  4. customdried
  5. customevaporated
  6. customAfter purification by preparative HPLC

出典と根拠

ORDレコード
ord-31c921d7ce224a1fae567d02eb829044
出典データセット
uspto-grants-2014_06
特許番号
US08748436B2

反応ノート

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