HCID 66782351, compound → HCID 66781655, compound

HRID 2242284Notes

Reaction equation

HRID 2242284 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][N:11]([CH2:46][CH:47](OCC)OCC)[C:12]([CH:14]([NH:27][C:28](=[O:45])[CH2:29][CH:30]([NH:34][C:35]([NH:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:36])[CH2:31][CH:32]=[CH2:33])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22]C(C)(C)C)=[CH:18][CH:17]=3)=[O:13])[C:4]=2[N:3]=[CH:2]1>C(O)=O>[CH2:38]([NH:37][C:35]([N:34]1[CH:30]([CH2:31][CH:32]=[CH2:33])[CH2:29][C:28](=[O:45])[N:27]2[CH:14]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)[C:12](=[O:13])[N:11]([CH2:10][C:9]3[C:4]4[N:3]=[CH:2][S:1][C:5]=4[CH:6]=[CH:7][CH:8]=3)[CH2:46][CH:47]12)=[O:36])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

3

Reactant 1

HCID 66782351HCID 66782351, compound

Product 1

HCID 66781655HCID 66781655, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of crude 3-(3-Benzyl-ureido)-hex-5-enoic acid [1-[benzothiazol-4-ylmethyl-(2,2-diethoxy-ethyl)-carbamoyl]-2-(4-tert-butoxy-phenyl)-ethyl]-amide (3.67 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 2-Allyl-8-benzothiazol-4-ylmethyl-6-(4-hydroxy-benzyl)-4,7-dioxo-hexahydro-pyrazino[1,2-a]pyrimidine-1-carboxylic acid benzylamide (1.2 g, 3 step yield: 35%). 1H NMR (CDCl3, 300 MHz) δ 9.20 (s, 1H), 7.4˜7.26 (m, 3H), 7.2 (d, J=7.01, 2H), 6.98 (t, J=8.0, 1H), 6.80 (m, 3H), 6.75 (t, J=7.0, 1H), 6.5 (d, J=8.76, 2H), 5.6 (m, 1H), 5.25 (t, J=4.7, 1H), 5.05 (d, J=10.75, 1H), 5.0 (d, J=18.54, 1H), 4.87 (d, J=14.51, 1H), 4.55 (m, 1H), 4.5˜4.25 (m, 4H), 3.5˜3.3 (m, 2H), 3.25˜3.1 (m, 2H), 2.6˜2.4 (m, 23H), 2.2 (t, J=7.2, 2H) MS ESI 596 (M+H), 618 (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-7faa8139b32a4121b64e0eca5103ffa8
Source dataset
uspto-grants-2010_03
Patent number
US07671054B1

Reaction notes

Loading…