Ethyl isocyanatoacetate → HCID 178525917, compound

HRID 2410056Notes

Reaction equation

HRID 2410056 reaction equation
[CH:1]1([CH2:4][CH2:5][N:6]2[C:11]([OH:12])=[C:10]([C:13]([NH:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14])[C:9](=[O:20])[N:8]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=3)[C:7]2=[O:30])[CH2:3][CH2:2]1.C1(CCN2C(=O)CC(=O)N(C3C=CC=C([N+]([O-])=O)C=3)C2=O)CC1.C(N(C(C)C)CC)(C)C.N(CC(OCC)=O)=C=O>ClCCl>[CH:1]1([CH2:4][CH2:5][N:6]2[C:11](=[O:12])[C:10]([C:13]([NH:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14])=[C:9]([OH:20])[N:8]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=3)[C:7]2=[O:30])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 76283Ethyl isocyanatoacetateHCID 81531DiisopropylethylamineHCID 59313196HCID 59313196, compoundHCID 68636488HCID 68636488, compound

Product 1

HCID 178525917HCID 178525917, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-{[1-(2-Cyclopropylethyl)-6-hydroxy-3-(3-nitrophenyl)-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycine. A mixture 1-(2-cyclopropylethyl)-3-(3-nitrophenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione (1.66 g, 5.23 mmole) and diisopropylethylamine (1.80 mL, 10.5 mmoles) in dichloromethane (80 mL) was treated with ethyl isocyanatoacetate (704 uL, 6.27 mmoles) and stirred overnight. The mixture was washed with 1 molar hydrochloric acid (×2), dried and evaporated. The residue was dissolved in ethanol (6 mL) and treated with 6 molar sodium hydroxide (5.0 mL). The mixture was stirred for 1 hour, acidified and extracted with ethyl acetate (×2), dried and evaporated. A solid was obtained from acetic acid-water, which was purified by trituration in boiling chloroform to give the title compound (800 mg, 37%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.12 (br. s, 1 H), 10.03 (s, 1 H), 8.35 (s, 1 H), 8.32 (ddd, J=8.40, 1.64, 1.33 Hz, 1 H), 7.82-7.88 (m, 1 H), 7.79 (t, J=8.08 Hz, 1 H), 4.14 (d, J=5.81 Hz, 2 H), 3.88-3.97 (m, 2 H), 1.50 (q, J=7.16 Hz, 2 H), 0.66-0.76 (m, 1 H), 0.42 (ddd, J=7.96, 5.68, 4.04 Hz, 2 H), 0.05 (td, J=5.18, 4.29 Hz, 2 H).

Workup

  1. washThe mixture was washed with 1 molar hydrochloric acid (×2)
  2. customdried
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethanol (6 mL)
  5. additiontreated with 6 molar sodium hydroxide (5.0 mL)
  6. stirringThe mixture was stirred for 1 hour
  7. extractionextracted with ethyl acetate (×2)
  8. customdried
  9. customevaporated
  10. customA solid was obtained from acetic acid-water, which
  11. customwas purified by trituration

Sources & evidence

ORD record
ord-2b18cb872fcf45949f23965c1e4c746f
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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