Carbonic acid, bis(1,1-dimethylethyl) ester → Ethyl-2-allyl-2-(tert-butoxycarbonylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate

HRID 579490노트

반응식

HRID 579490 반응식
[CH2:1]([C:4]([NH2:23])([CH2:10][CH2:11][CH2:12][CH2:13][B:14]1[O:18][C:17]([CH3:20])([CH3:19])[C:16]([CH3:22])([CH3:21])[O:15]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:2]=[CH2:3].[C:24](=O)([O:30]C(C)(C)C)[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]>C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[CH2:1]([C:4]([NH:23][C:24]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:30])([CH2:10][CH2:11][CH2:12][CH2:13][B:14]1[O:15][C:16]([CH3:22])([CH3:21])[C:17]([CH3:20])([CH3:19])[O:18]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:2]=[CH2:3]

참가 물질

5

반응물 2

HCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 66833537Ethyl 2-allyl-2-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate

생성물 1

HCID 66833330Ethyl-2-allyl-2-(tert-butoxycarbonylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate수율 82%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

A solution of ethyl 2-allyl-2-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (0.0897 g, 0.276 mmol) in ethyl acetate (0.6 mL, 0.5 M) and saturated aqueous NaHCO3 (0.6 mL) was treated with di-tert-butyl carbonate (0.090 g, 0.414 mmol) and stirred at room temperature. After 16 h, the layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. Purification by MPLC (0-20% ethyl acetate in heptane over 6 CV) gave ethyl 2-allyl-2-(tert-butoxycarbonylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate as a colorless oil (0.096 g, 82%). Rf 0.53 (30% ethyl acetate in heptane); ESI-LCMS m/z calcd for C22H40BNO6: 425.3. found 426.3 (M+H)+.

후처리

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by MPLC (0-20% ethyl acetate in heptane over 6 CV)

출처 및 근거

ORD 기록
ord-961072422f444ef5832b100cd4a6bb81
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040703B2

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