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

HRID 1037962노트

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HRID 1037962 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-09f7bb4446ae4e9d98bb247ad65d9738
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546588B2

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