Diethyl Ether → Methyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)thiazole-5-carboxylate

HRID 1037962ノート

反応式

HRID 1037962 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[S:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][N:15]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][Si](C=[N+]=[N-])(C)C.CCOCC>CO.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[S:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:15]=1)[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 673960092-(1-{[(Tert-butoxy)carbonyl]amino}ethyl)-1,3-thiazole-5-carboxylic acid

生成物 1

HCID 67397774Methyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)thiazole-5-carboxylate収率 83%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-(1-(tert-butoxycarbonylamino)ethyl)thiazole-5-carboxylic acid (1.03 g, 3.8 mmol) in a mixture of MeOH (20 mL) and toluene (20 mL) cooled to 0° C. was added dropwise 2.0M trimethylsilyldiazomethane in ether (12 mL, 24 mmol). The resulting reaction mixture was warmed to room temperature overnight. Excess trimethylsilyldiazomethane was quenched with the addition of acetic acid and the solution concentrated to dryness. The residue was partitioned between EtOAc and saturated aqueous NaHCO3, the organic layer dried over anhydrous Mg2SO4 and concentrated to afford a yellow oil (0.90 g, 83%). LC-MS: (FA) ES+ 287.

後処理

  1. customThe resulting reaction mixture
  2. temperaturewas warmed to room temperature overnight
  3. customExcess trimethylsilyldiazomethane was quenched with the addition of acetic acid
  4. concentrationthe solution concentrated to dryness
  5. customThe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  6. dry with materialthe organic layer dried over anhydrous Mg2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-09f7bb4446ae4e9d98bb247ad65d9738
出典データセット
uspto-grants-2013_10
特許番号
US08546588B2

反応ノート

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