Sodium sulfate decahydrate → (R)-tert-butyl 1-(4-(hydroxymethyl)oxazol-2-yl)ethylcarbamate

HRID 245939노트

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HRID 245939 반응식
C[O:2][C:3]([C:5]1[N:6]=[C:7]([C@H:10]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:11])[O:8][CH:9]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[C:16]([O:15][C:13](=[O:14])[NH:12][C@@H:10]([C:7]1[O:8][CH:9]=[C:5]([CH2:3][OH:2])[N:6]=1)[CH3:11])([CH3:17])([CH3:18])[CH3:19]

참가 물질

5

반응물 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 68671221(R)-methyl 2-(1-(tert-butoxycarbonylamino)ethyl)oxazole-4-carboxylate

생성물 1

HCID 68670262(R)-tert-butyl 1-(4-(hydroxymethyl)oxazol-2-yl)ethylcarbamate수율 103.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

In a round-bottomed flask, 2-((R)-1-tert-butoxycarbonylamino-ethyl)-oxazole-4-carboxylic acid methyl ester (151 mg, 0.56 mmol) was dissolved in THF (4 ml). The pale yellow solution was cooled to 0° C. and lithium aluminum hydride (1.0 M in THF, 0.60 ml, 0.60 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1.5 h then sodium sulfate decahydrate was carefully added. When gas evolution had ceased, the ice bath was removed, sodium sulfate was added and the mixture was stirred vigorously for 30 min at room temperature. The suspension was filtered over Celite and rinsed with ethyl acetate/methanol. The filtrate was concentrated to give 140 mg (93%) of [(R)-1-(4-hydroxymethyl-oxazol-2-yl)-ethyl]-carbamic acid tert-butyl ester as yellow oil which was used without further purification.

후처리

  1. customthe ice bath was removed
  2. additionsodium sulfate was added
  3. stirringthe mixture was stirred vigorously for 30 min at room temperature
  4. filtrationThe suspension was filtered over Celite
  5. washrinsed with ethyl acetate/methanol
  6. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-278991eb5df74b4c81db848bd5717321
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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