HCID 86644984, compound → HCID 66782422, compound

HRID 1096534Notes

Reaction equation

HRID 1096534 reaction equation
[CH2:1]([N:8]([CH2:25][CH:26](OCC)OCC)[C:9]([CH:11]([NH2:24])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19]C(C)(C)C)=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([NH:40][C:41](=[O:51])[NH:42][CH:43]([CH2:48]C=C)[CH2:44][C:45](O)=[O:46])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(O)=O>[CH2:33]([NH:40][C:41]([N:42]1[CH:43]([CH3:48])[CH2:44][C:45](=[O:46])[N:24]2[CH:11]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)[C:9](=[O:10])[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:25][CH:26]12)=[O:51])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

3

Reactant 1

HCID 86644984HCID 86644984, compound

Product 1

HCID 66782422HCID 66782422, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of crude 3-(3-Benzyl-ureido)-hex-5-enoic acid [1-[benzyl-(2,2-diethoxy-ethyl)-carbamoyl]-2-(4-tert-butoxy-phenyl)-ethyl]-amine (3.26 g, 4.95 mmol) in formic acid (100 mL) was stirred at room temperature for 13 h. The solvent was removed under reduced pressure and then diluted with EtOAc, washed with water and brine. The organic layer was dried with Na2SO4 and concentrated in vacuo. The residue was purified by chromatography and recrystallized on ethyl acetate and hexane to give the 8-Benzyl-6-(4-hydroxy-benzyl)-2-methyl-4,7-dioxo-hexahydro-pyrazino[1,2-a]pyrimidine-1-carboxylic acid benzylamide (1.12 g, 3 step yield: 38%). 1H NMR (CDCl3, 300 MHz) δ 7.5˜7.3 (m, 5H), 7.2 (d, J=7.01, 2H), 6.80 (m, 5H), 6.5 (d, J=8.76, 2H), 5.6 (m, 1H), 5.25 (t, J=4.7, 1H), 4.55 (m, 1H), 4.5˜4.25 (m, 4H, OH), 3.5˜3.3 (m, 2H), 3.25-3.1 (m, 2H), 2.2 (t, J=7.2, 2H) 1.36 (m, 3H) MS ESI 513 (M+H), 535 (M+Na).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additiondiluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography
  7. customrecrystallized on ethyl acetate and hexane

Sources & evidence

ORD record
ord-93bc5774f6db4ae59deea21bef561716
Source dataset
uspto-grants-2012_03
Patent number
US08138337B2

Reaction notes

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