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Triethylamine → (9-(3-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

HRID 471018
ノート
印刷プレビュー

反応式

HRID 471018 の反応式
FC(F)(F)C(O)=O.[CH:8]([C:11]1[S:12][CH:13]=[C:14]([C:16]([N:18]2[CH2:23][C:22]3([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[O:21][CH2:20][CH2:19]2)=[O:17])[N:15]=1)([CH3:10])[CH3:9].Br[CH2:30][C:31]1[CH:32]=[C:33]([CH2:37][CH2:38][OH:39])[CH:34]=[CH:35][CH:36]=1.C(N(CC)CC)C>C(#N)C>[OH:39][CH2:38][CH2:37][C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][CH:34]=1)[CH2:30][N:26]1[CH2:25][CH2:24][C:22]2([O:21][CH2:20][CH2:19][N:18]([C:16]([C:14]3[N:15]=[C:11]([CH:8]([CH3:10])[CH3:9])[S:12][CH:13]=3)=[O:17])[CH2:23]2)[CH2:28][CH2:27]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 18999576Benzeneethanol, 3-(bromomethyl)-HCID 66964182(2-Isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

生成物 1

HCID 57989126(9-(3-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of (2-isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 22, step b) (0.85 g) and 2-(3-(bromomethyl)phenyl)ethanol (example 6, step a) (0.432 g) in acetonitrile (10 mL) at 20° C. was treated with triethylamine (0.616 mL) and then stirred for 2 hours. The solvent was evaporated under reduced pressure and the residue partitioned between ethyl acetate and brine, the organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 1% triethylamine and 3% methanol in dichloromethane. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.71 g.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and brine
  3. dry with materialthe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography, elution gradient 1% triethylamine and 3% methanol in dichloromethane
  7. customPure fractions were evaporated to dryness

出典と根拠

ORDレコード
ord-fb021460c82947818441a48d72c0549c
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08629271B2

反応ノート

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