Diisobutylaluminum hydride → Tert-butyl ((4-(hydroxymethyl)oxazol-2-yl)methyl)carbamate

HRID 1157849

반응식

HRID 1157849 반응식
C[O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[O:8][CH:9]=1)=O.CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>ClCCl>[C:15]([O:14][C:12](=[O:13])[NH:11][CH2:10][C:7]1[O:8][CH:9]=[C:5]([CH2:3][OH:2])[N:6]=1)([CH3:18])([CH3:16])[CH3:17]

참가 물질

5

반응물 3

HCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 11065028Methyl 2-((tert-butoxycarbonylamino)methyl)oxazole-4-carboxylate

생성물 1

HCID 20725635Tert-butyl ((4-(hydroxymethyl)oxazol-2-yl)methyl)carbamate수율 28.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

The ester (178 mg, 0.695 mmol) in 0° C. dichloromethane (8 mL) was treated with DIBAL-H (1 M in dichloromethane, 2.08 mL, 2.08 mmol). The mixture was then stirred at 0° C. for 2 hours before being treated with aqueous 5% sodium potassium tartrate (8 mL). The mixture was stirred rapidly for 30 minutes (until the aqueous and organic layers clarified), and the layers were then separated. The aqueous layer was extracted twice with dichloromethane. The combined organic fractions were then dried over anhydrous sodium sulfate and concentrated. Purification by chromatography on silica gel (5% methanol in dichloromethane) gave (4-hydroxymethyl-oxazol-2-ylmethyl)-carbamic acid tert-butyl ester as an oil (45 mg, 28%). 1H NMR (CDCl3) δ 1.40 (s, 9H), 4.43 (d, 2H, J=5.6 Hz), 4.56 (s, 2H), 5.37 (s, 1H), 7.54 (s, 1H).

후처리

  1. stirringThe mixture was stirred rapidly for 30 minutes (until the aqueous and organic layers
  2. customwere then separated
  3. extractionThe aqueous layer was extracted twice with dichloromethane
  4. dry with materialThe combined organic fractions were then dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customPurification by chromatography on silica gel (5% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-f816e08cdf00484586c4294ef4fd71e8
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807694B2

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