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 579490ノート

反応式

HRID 579490 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-961072422f444ef5832b100cd4a6bb81
出典データセット
uspto-grants-2015_05
特許番号
US09040703B2

反応ノート

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