Diethylamine → HCID 131717794, compound

HRID 1612814Notes

Reaction equation

HRID 1612814 reaction equation
[CH2:1]([C@H:10]1[O:12][C@H:11]1[C:13](O)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH2:16]([N:18]([CH2:21][CH3:22])[CH2:19]C)[CH3:17].C([O:27]C(Cl)=O)C(C)C.C(NCC)C>C1COCC1.CCOCC>[CH2:16]([N:18]([CH2:21][CH3:22])[C:19]([CH2:13][C@@H:11]1[C@H:10]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[O:12]1)=[O:27])[CH3:17]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 53842677HCID 53842677, compound

Product 1

HCID 131717794HCID 131717794, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 75 mg 90.35 mmole) of (2R-cis)-3-nonyloxiranecarboxylic acid and 0.148 ml (106 mg, 1.05 mmole) of triethylamine in 5 ml of THF was prepared under argon and cooled to 0° C. To this solution 50 mg (0.37 mmole) of isobutylchloroformate was added and the mixture was allowed to stir of 30 min. Diethylamine (0.109 ml, 76 mg, 1.05 mmole) was then added and the mixture stirred for an additional 2 hours. The reaction was diluted with 75 ml of Et2O, washed with 50 ml of saturated NaHCO3, 30 ml of brine, dried over MgSO4, filtered and evaporated to yield a clear residue. This residue was flash chromatographed (25 mm column; 5% MeOH:CHCl3) to afford 80 mg of a clear oil. 1H NMR 3.57 (d, 1, J=4 Hz), 3.6-3.3 (m, 4), 3.2 (m, 1), 1.6-1.2 (m, 19), 1.13 (t, 3, J=7 Hz), 0.88 (t, 3, J=7 Hz). Mass Spectra: M+(1.5)269, M-OH(1.3)252, M(100)100.1.

Workup

  1. stirringthe mixture stirred for an additional 2 hours
  2. washwashed with 50 ml of saturated NaHCO3, 30 ml of brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto yield a clear residue
  7. customchromatographed (25 mm column; 5% MeOH:CHCl3)

Sources & evidence

ORD record
ord-d25de8b3c76f4b3dbb0310c63534372c
Source dataset
uspto-grants-1993_03
Patent number
US05190969

Reaction notes

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