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Toluene → 3-(2-Chloro-3-((4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoic acid

HRID 446449
ノート
印刷プレビュー

反応式

HRID 446449 の反応式
[Cl:1][C:2]1[C:19]([CH2:20][N:21]2[CH2:40][CH2:39][C:24]3([O:29][CH2:28][CH2:27][N:26]([C:30]([C:32]4[N:33]=[C:34]([CH2:37][CH3:38])[S:35][CH:36]=4)=[O:31])[CH2:25]3)[CH2:23][CH2:22]2)=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][CH2:5][O:6][CH2:7][CH2:8][C:9]([O:11]C(C)(C)C)=[O:10].FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[C:19]([CH2:20][N:21]2[CH2:22][CH2:23][C:24]3([O:29][CH2:28][CH2:27][N:26]([C:30]([C:32]4[N:33]=[C:34]([CH2:37][CH3:38])[S:35][CH:36]=4)=[O:31])[CH2:25]3)[CH2:39][CH2:40]2)=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][CH2:5][O:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]
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 1140TolueneHCID 6422Trifluoroacetic acid2 回HCID 58168518Tert-butyl 3-(2-chloro-3-((4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoate

生成物 1

HCID 581684923-(2-Chloro-3-((4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoic acid収率 200%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

A solution of tert-butyl 3-(2-chloro-3-((4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanoate (limiting reagent) (step d) in DCM (2.8 volumes) was cooled to 5° C. Trifluoroacetic acid (10 molar equivalents) was added over 20 min (exotherm to 15° C.). The reaction mixture was warmed to ambient and stirred for 18 hr, Toluene (3 volumes) was added and the mixture was evaporated. The resulting gum was triturated with toluene (2×1.5 volumes) and evaporated to give a brown gum. Yield: 200% of theoretical. (carried through crude—NMR assay shows ˜45% by weight purity with remaining weight due to TFA trapped in the gum)

後処理

  1. temperatureThe reaction mixture was warmed to ambient and
  2. customthe mixture was evaporated
  3. customThe resulting gum was triturated with toluene (2×1.5 volumes)
  4. customevaporated
  5. customto give a brown gum

出典と根拠

ORDレコード
ord-2cdd0fe0a6ee4216a73c6fe418cf8bdc
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08476265B2

反応ノート

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