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 579490Notes

Reaction equation

HRID 579490 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-961072422f444ef5832b100cd4a6bb81
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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