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

HRID 579515

Reaction equation

HRID 579515 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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)]

Workup

  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)

Sources & evidence

ORD record
ord-45e3041e8c664d99b721b686446a0fe3
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Linked notes

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