Acetic acid, 2-isothiocyanato-, ethyl ester → HCID 135849831, compound

HRID 2410053Notes

Reaction equation

HRID 2410053 reaction equation
[CH:1]1([N:7]2[C:12](=[O:13])[CH2:11][C:10](=[O:14])[N:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])[C:8]2=[O:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[N:35]([CH2:38][C:39]([O:41]CC)=[O:40])=[C:36]=[S:37]>C(Cl)(Cl)Cl>[C:39]([CH2:38][NH:35][C:36]([C:11]1[C:12](=[O:13])[N:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:8](=[O:25])[N:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:10]=1[OH:14])=[S:37])([OH:41])=[O:40]

Participants

5

Reactant 3

HCID 32202Acetic acid, 2-isothiocyanato-, ethyl esterHCID 81531DiisopropylethylamineHCID 68636634HCID 68636634, compound

Product 1

HCID 135849831HCID 135849831, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of ethyl 6-(3-cyclohexyl-2,4,6-trioxotetrahydro-1(2H)-pyrimidinyl)hexanoate (330 mg, 0.94 mmoles), diisopropylethylamine (324 uL, 1.87 mmoles) and ethyl isothiocyanatoacetate (139 uL, 1.12 mmoles) in chloroform (20 mL) was stirred for 7 days. The mixture was washed with 1 molar hydrochloric acid (×2), dried and evaporated. The residue was purified by flash chromatography (hexane-20% ethyl acetate in hexane) to give the title compound as a clear oil (250 mg, 60%). The diester was dissolved in ethanol (3 mL) and treated with 1 molar sodium hydroxide (2 mL). The mixture was stirred overnight, taken up in ethyl acetate and washed with 1 molar hydrochloric acid (×2), dried and evaporated. Crystallization from acetic acid afforded the title compound (160 mg, 40%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.13 (br s, 1 H), 12.50 (s, 1 H), 12.03 (br s, 1 H), 4.71 (m, 1 H), 4.35 (d, J=5.05 Hz, 2H), 3.84 (t, J=7.20 Hz, 2 H), 2.10-2.38 (m, 4 H), 1.80 (d, J=12.63 Hz, 2 H), 1.42-1.71 (m, 7 H), 1.21-1.42 (m, 4 H), 1.01-1.22 (m, 1 H).

Workup

  1. washThe mixture was washed with 1 molar hydrochloric acid (×2)
  2. customdried
  3. customevaporated
  4. customThe residue was purified by flash chromatography (hexane-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4fca9d7a491640d6a3d0c5ab12387103
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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