Potassium Carbonate → Ethyl 2-(tert-butoxycarbonylamino)-2-(hydroxymethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate

HRID 579515

Reaktionsgleichung

Reaktionsgleichung von HRID 579515
C([O:4][CH2:5][C:6]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([CH2:12][CH2:13][CH2:14][CH2:15][B:16]1[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:29]([O:28][C:26]([NH:25][C:6]([CH2:5][OH:4])([CH2:12][CH2:13][CH2:14][CH2:15][B:16]1[O:17][C:18]([CH3:24])([CH3:23])[C:19]([CH3:22])([CH3:21])[O:20]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:27])([CH3:32])([CH3:30])[CH3:31]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 66832797Ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate

Produkt 1

HCID 66833197Ethyl 2-(tert-butoxycarbonylamino)-2-(hydroxymethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-(acetoxymethyl)-2-(tert-butoxycarbonylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (12.0 g, 26.3 mmol) in ethanol (100 mL) was treated with solid potassium carbonate (3.62 g, 26.3 mmol) and stirred for 2 h. The solution was filtered and the filtrate was evaporated to dryness. The resulting residue was dissolved in ethyl acetate (150 mL) and washed successively with water (50 mL) and saturated aqueous sodium chloride (50 mL). Organic layer was concentrated and purified using a combiflash system (120 g column, eluting with 20-30% ethyl acetate in heptanes) to give ethyl 2-(tert-butoxycarbonylamino)-2-(hydroxymethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (7.0 g, 78%). 1H NMR (CDCl3) δ 5.25 (bs, 1H), 4.00 (m, 2H), 3.91 (d, J=11.3 Hz, 1H), 3.60 (d, J=11.3 Hz, 1H), 1.53-1.46 (m, 1H), 1.23 (s, 9H), 1.21-1.15 (m, 1H), 1.06 (m, 7H), 1.03 (s, 12H), 0.90 (m, 1H), 0.54 (t, J=7.8 Hz, 2H). MS found for C20H38BNO7 m/z[438(M+Na)]

Aufarbeitung

  1. filtrationThe solution was filtered
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe resulting residue was dissolved in ethyl acetate (150 mL)
  4. washwashed successively with water (50 mL) and saturated aqueous sodium chloride (50 mL)
  5. concentrationOrganic layer was concentrated
  6. custompurified
  7. washa combiflash system (120 g column, eluting with 20-30% ethyl acetate in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-45e3041e8c664d99b721b686446a0fe3
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040703B2

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