Water → HCID 13496994, compound

HRID 714272Notes

Reaction equation

HRID 714272 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[C-:2].C1CCN2C(=NCCC2)CC1.[C:20](Cl)(=[O:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>CN(C=O)C>[CH2:21]([C:20]1[O:27][CH:2]=[N:1][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 17313Heptanoyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 533707Ethyl isocyanoacetate

Product 1

HCID 13496994HCID 13496994, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 2-isocyanoacetate (1.0 g, 8.84 mmol) was dissolved in DMF (5 mL) in a 25 mL 1 neck pear shaped flask that was equipped with a magnetic stirrer and an Ar inlet. DBU (1.999 mL, 13.26 mmol) and heptanoyl chloride (1.770 mL, 11.49 mmol) were added and the reaction mixture was stirred at 80° C. for 6 h. The reaction mixture was poured into water (50 mL) and extracted with EtOAc (3×30 mL). The phases were separated and the organic phase was dried over MgSO4 and concentrated in vacuo to a a dark oil. The desired product was isolated by distillation at 90-95° C. at 0.3 mmHg as a clear oil (0.89 g, 45%). LCMS Anal. Calc'd for C12H19NO3 225.1. found [M+H] 226.1. 1H NMR (500 MHz, CDCl3) δ 7.76 (s, 1H), 4.37 (q, J=7.2 Hz, 2H), 3.03 (t, J=7.6 Hz, 2H), 1.71-1.64 (m, 2H), 1.38 (t, J=7.2 Hz, 3H), 1.35-1.26 (m, 6H), 0.86 (t, J=6.3 Hz, 3H).

Workup

  1. customwas equipped with a magnetic stirrer
  2. extractionextracted with EtOAc (3×30 mL)
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo to a a dark oil

Sources & evidence

ORD record
ord-b9ba5de6940141729beaa72378d82ffd
Source dataset
uspto-grants-2015_11
Patent number
US09187424B1

Reaction notes

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