Acetic Acid → HCID 178473813, compound

HRID 2410062Notes

Reaction equation

HRID 2410062 reaction equation
[CH:1]1([N:7]2[C:12](=[O:13])[C:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])=[C:10]([OH:21])[N:9]([CH:22]3[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]3)[C:8]2=[O:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:29](O)(=[O:31])[CH3:30]>C(OC(=O)C)(=O)C.C(OCC)(=O)C>[C:29]([N:24]1[CH2:25][CH2:26][CH2:27][CH:22]([N:9]2[C:10]([OH:21])=[C:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])[C:12](=[O:13])[N:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:8]2=[O:28])[CH2:23]1)(=[O:31])[CH3:30]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 178525918HCID 178525918, compound

Product 1

HCID 178473813HCID 178473813, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-{[3-cyclohexyl-6-hydroxy-2,4-dioxo-1-(3-piperidinyl)-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycine (500 mg, 1.26 mmoles) in acetic acid (5.0 mL) and acetic anhydride (5.0 mL) was heated at 130° C. for 2 hours. The mixture was cooled, diluted with ethyl acetate and washed with 1 molar hydrochloric acid (×3), dried and evaporated. Flash chromatography (dichloromethane to 4% methanol-0.1% acetic acid in dichloromethane) and recrystallization from ethanol-water gave the title compound (170 mg, 31%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.10 (br. s., 1 H), 10.17 (s, 1 H), 4.46-4.73 (m, 2 H), 4.25-4.46 (m, 1H), 4.13 (d, J=5.56 Hz, 2 H), 3.67-3.92 (m, J=4.55 Hz, 1 H), 3.24-3.43 (m, 1 H), 2.94 (t, J=12.63 Hz, 1 H), 2.34-2.48 (m, 1 H), 2.25 (m, 2 H), 1.97, 2.02 (2×s, 3 H), 1.69-1.87 (m, 4 H), 1.62 (m, 3 H), 1.41-1.57 (m, 1 H), 1.19-1.37 (m, 2 H), 0.97-1.18 (m, 1 H)

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with 1 molar hydrochloric acid (×3)
  3. customdried
  4. customevaporated
  5. customFlash chromatography (dichloromethane to 4% methanol-0.1% acetic acid in dichloromethane) and recrystallization from ethanol-water

Sources & evidence

ORD record
ord-33a9c0a5d8574180afadbb39fa43653d
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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