Ethyl isocyanatoacetate → HCID 24830240, compound

HRID 2410045Notes

Reaction equation

HRID 2410045 reaction equation
[CH3:1][CH:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:10](=[O:11])[CH2:9][C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:6]1=[O:18].C(N(C(C)C)CC)(C)C.[N:29]([CH2:32][C:33]([O:35]CC)=[O:34])=[C:30]=[O:31]>ClCCl>[OH:11][C:10]1[N:5]([CH2:4][CH2:3][CH:2]([CH3:19])[CH3:1])[C:6](=[O:18])[N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:8](=[O:12])[C:9]=1[C:30]([NH:29][CH2:32][C:33]([OH:35])=[O:34])=[O:31]

Participants

5

Reactant 3

HCID 76283Ethyl isocyanatoacetateHCID 81531DiisopropylethylamineHCID 18375361HCID 18375361, compound

Product 1

HCID 24830240HCID 24830240, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

-{[6-Hydroxy-1,3-bis(3-methylbutyl)-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycine. A mixture of 1,3-bis(3-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione (1.2 g, 4.47 mmoles) and diisopropylethylamine (1.56 mL, 8.94 mmoles) was stirred in dichloromethane (30 mL) and treated with ethyl isocyanatoacetate (501 uL, 4.47 mmoles). The mixture was stirred for 5 hours, washed with 1 molar hydrochloric acid (×2), evaporated, taken up in ethanol-6 molar sodium hydroxide and stirred overnight. The mixture was acidified and extracted into ethyl acetate (×2). The extracts were washed with 1 molar hydrochloric acid evaporated, dried and evaporated. The title compound was recrystallized from acetic acid (430 mg, 26%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.09 (br. s, 1 H), 10.11 (s, 1 H), 4.09-4.16 (m, 2 H), 3.77-3.86 (m, 4 H), 1.51-1.62 (dt, J=13.29, 6.59, 6.59, 6.59, 6.59 Hz, 2 H), 1.42 (q, J=7.07 Hz, 4 H), 0.91 (d, J=6.57 Hz, 12 H).

Workup

  1. washwashed with 1 molar hydrochloric acid (×2)
  2. customevaporated
  3. stirringstirred overnight
  4. extractionextracted into ethyl acetate (×2)
  5. washThe extracts were washed with 1 molar hydrochloric acid
  6. customevaporated
  7. customdried
  8. customevaporated
  9. customThe title compound was recrystallized from acetic acid (430 mg, 26%)

Sources & evidence

ORD record
ord-6e7e951143ab4f6aae06267469ccbb34
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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