Solketal → HCID 86612334, compound

HRID 1517634Notes

Reaction equation

HRID 1517634 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[O:10]=[C:11]1[CH2:15][CH2:14][C:13](=[O:16])[N:12]1[O:17][C:18](=O)[O:19]N1C(=O)CCC1=O.C(N(CC)CC)C>C(#N)C>[O:10]=[C:11]1[CH2:15][CH2:14][C:13](=[O:16])[N:12]1[O:17][C:18](=[O:19])[O:8][CH2:7][CH:5]1[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]1

Participants

5

Reactant 3

HCID 7528SolketalHCID 8471TriethylamineHCID 676246Di(succinimido) carbonate

Product 1

HCID 86612334HCID 86612334, compoundYield 122%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (0.4 g, 3.0 mmol) in acetonitrile (10 mL) was added carbonic acid bis-(2,5-dioxo-pyrrolidin-1-yl) ester (1.15 g, 4.5 mmol) and triethylamine (0.84 mL, 6.0 mmol). After stirring at ambient temperature for 10 min, the mixture was concentrated at reduced pressure, sat. NaHCO3 (50 mL)was added, and the solution was extracted with ethyl acetate and organic phase was separated and concentrated to obtain 1.0 g of crude product that was used without further purification in the next step. MS (APCI) m/z: 273 [M+H]+ 1H NMR (DMSO-d6) δ: 4.50 (m, 1H), 4.40-4.29 (m, 2H), 4.04 (m, 1H), 3.73 (dd, J=6.0 and 9.0 Hz, 1H), 2.80 (s, 4H), 1.35 (s, 3H), 1.30 (s, 3H).

Workup

  1. concentrationthe mixture was concentrated at reduced pressure, sat. NaHCO3 (50 mL)
  2. additionwas added
  3. extractionthe solution was extracted with ethyl acetate and organic phase
  4. customwas separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4de78232db5147a796b5e8b540a51478
Source dataset
uspto-grants-2012_07
Patent number
US08232309B2

Reaction notes

Loading…