Ethyl isocyanatoacetate → HCID 178448687, compound

HRID 2410031Notes

Reaction equation

HRID 2410031 reaction equation
[OH:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4](=[O:19])[C:3]=1[C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21].[CH2:27](N1C(=O)CC(=O)N(CC2C=CC=CC=2)C1=O)CCC.C(N(C(C)C)CC)(C)C.N(CC(OCC)=O)=C=O>C(Cl)(Cl)Cl>[CH2:8]([N:7]1[C:2]([OH:1])=[C:3]([C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21])[C:4](=[O:19])[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]1=[O:11])[CH2:9][CH2:10][CH3:27]

Participants

6

Reactant 4

HCID 76283Ethyl isocyanatoacetateHCID 81531DiisopropylethylamineHCID 68635486HCID 68635486, compoundHCID 178456543HCID 178456543, compound

Product 1

HCID 178448687HCID 178448687, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-{[6-Hydroxy-2,4-dioxo-3-(phenylmethyl)-1-propyl-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycine. A solution of 1-butyl-3-(phenylmethyl)-2,4,6(1H,3H,5H)-pyrimidinetrione (676 mg, 2.46 mmoles) and diisopropylethylamine (826 uL, 4.93 mmoles) in chloroform (12 mL) was treated with ethyl isocyanatoacetate (211 uL, 2.46 mmoles) and stirred for 3 hours under argon. The mixture was washed with 1 molar hydrochloric acid (×2), dried and evaporated. The residue was dissolved in ethanol (10 mL), treated with 1 molar sodium hydroxide solution (7 mL) and stirred overnight. The mixture was acidified and extracted into ethyl acetate and the organic solution dried and evaporated. Crystallization from ethanol-water gave the title compound (580 mg, 63%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.10 (s, 1 H), 10.11 (s, 1 H), 7.24-7.35 (m, 5 H), 5.01 (s, 2 H), 4.13 (d, J=5.81 Hz, 2 H), 3.79-3.87 (m, 2 H), 1.54 (dq, J=7.58, 7.41 Hz, 2 H), 1.29 (dq, J=14.97, 7.39 Hz, 2 H), 0.89 (t, J=7.45 Hz, 3 H).

Workup

  1. washThe mixture was washed with 1 molar hydrochloric acid (×2)
  2. customdried
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethanol (10 mL)
  5. additiontreated with 1 molar sodium hydroxide solution (7 mL)
  6. stirringstirred overnight
  7. extractionextracted into ethyl acetate
  8. customthe organic solution dried
  9. customevaporated
  10. customCrystallization from ethanol-water

Sources & evidence

ORD record
ord-3d5b5d461dde4cb3a8cca44b794325ca
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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