Ethyl isocyanatoacetate → HCID 178440907, compound

HRID 2410019Notes

Reaction equation

HRID 2410019 reaction equation
[CH3:1][C:2]([N:5]1[C:10]([OH:11])=[C:9]([C:12]([NH:14][CH2:15][C:16]([O:18]CC)=[O:17])=[O:13])[C:8](=[O:21])[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=2)[C:6]1=[O:33])([CH3:4])[CH3:3].CC(N1C(=O)CC(=O)N(CC2C=CC(C(C)(C)C)=CC=2)C1=O)(C)C.C(N(C(C)C)CC)(C)C.N(CC(OCC)=O)=C=O>C(Cl)(Cl)Cl>[CH3:4][C:2]([N:5]1[C:10]([OH:11])=[C:9]([C:12]([NH:14][CH2:15][C:16]([OH:18])=[O:17])=[O:13])[C:8](=[O:21])[N:7]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:27][CH:28]=2)[C:6]1=[O:33])([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 76283Ethyl isocyanatoacetateHCID 81531DiisopropylethylamineHCID 68637037HCID 68637037, compoundHCID 178472772HCID 178472772, compound

Product 1

HCID 178440907HCID 178440907, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl N-[(1-(1,1-dimethylethyl)-3-{[4-(1,1-dimethylethyl)phenyl]methyl}-6-hydroxy-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)carbonyl]glycinate. 1-(1,1-Dimethylethyl)-3-{[4-(1,1-dimethylethyl)phenyl]methyl}-2,4,6(1H,3H,5H)-pyrimidinetrione (1.3 g, 3.93 mmoles) and diisopropylethylamine (1.36 mL, 7.86 mmoles) were stirred together in dry chloroform (25 mL) and treated with ethyl isocyanatoacetate (335 uL, 3.93 mmoles). The mixture was stirred for 3 hours, washed twice with 1 molar hydrochloric acid, dried and evaporated to give the title compound (1.8 g, quant.) 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.32 (t, J=7.07 Hz, 3 H) 1.71 (s, 9 H) 1.73 (s, 9 H) 4.28-4.34 (m, 2 H) 5.03-5.07 (m, 2 H) 7.33-7.39 (m, 4 H) 10.21-10.30 (m, 1 H).

Workup

  1. washwashed twice with 1 molar hydrochloric acid
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-7fcaa5baaf81493cb3c90bcc558e71b0
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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