Ethyl Acetate → HCID 140397803, compound

HRID 1859184Notes

Reaction equation

HRID 1859184 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([C:14]1[CH:32]=[CH:31][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][NH:26][C:25](=[O:29])[C:24]2=[O:30])=[CH:16][CH:15]=1)=[NH:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH:36]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:37]([O:39][CH:40]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38].C(OCC)(=O)C>CN(C)C=O.O>[CH2:1]([O:8][C:9]([NH:11][C:12]([C:14]1[CH:32]=[CH:31][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH:36]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C:37]([O:39][CH:40]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[O:38])[C:25](=[O:29])[C:24]2=[O:30])=[CH:16][CH:15]=1)=[NH:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 15101289HCID 15101289, compoundHCID 140397792HCID 140397792, compound

Product 1

HCID 140397803HCID 140397803, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 5 ml of N,N-dimethylformamide was dissolved 0.2 g of 1-[4-(4-benzyloxycarbonylamidinophenoxy)butyl]-2,3-dioxopiperazine, followed by adding thereto 20 mg of sodium hydride (60%, oil), and the resulting mixture was stirred at 50° C. for 30 minutes. The reaction mixture was cooled to room temperature and 0.17 g of diphenylmethyl α-bromophenylacetate was added thereto. After stirring at the same temperature for 2 hours, the reaction mixture was added to a mixed solvent of 20 ml of ethyl acetate and 20 ml of water. The organic layer was separated, washed with water and then a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=20:1) to obtain 0.29 g of diphenylmethyl α-[4-[4-(4-benzyloxycarbonylamidinophenoxy)butyl]-2,3-dioxopiperazin-1-yl]-α-phenylacetate as a colorless oil.

Workup

  1. additionby adding
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-3b96d47f6524480b88a4bb7f98e1c77a
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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