2-Chloroethyl methyl ether → HCID 13655579, compound

HRID 543258Notes

Reaction equation

[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[H-].[CH3:18][O:19][CH2:20][CH2:21]Cl>CN(C)C=O>[CH3:18][O:19][CH2:20][CH2:21][N:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 28.5 g (0.13 mol) of benzyl (L)-pyroglutamate, prepared according to Example II(1), in 200 ml of N,N-dimethylformamide is added over 1.5 hours to a suspension of 6.24 g (0.13 mol) of solution hydride in 30 ml of N,N-dimethylformamide. The mixture is stirred for 1 hour at ordinary temperature and a solution of 14.7 g (156 mmol) of 2-methoxyethyl chloride in 100 ml of dimethylformamide is then run in. The mixture is heated at 70° C. for 5 hours and stirred at ordinary temperature for 15 hours and evaporated to dryness, the residue is taken up with 200 ml of 0.5N hydrochloric acid, extraction is carried out with benzene and the extract is washed with water and dried. After evaporation of the benzene layer, the residue is purified by chromatography on a silica column using a methylene chloride/ether mixture as the eluent. This gives 45% of a pure product of Rf=0.45 (A).

Workup

stirringstirred at ordinary temperature for 15 hours
customevaporated to dryness
extractionthe residue is taken up with 200 ml of 0.5N hydrochloric acid, extraction
washthe extract is washed with water
customdried
customAfter evaporation of the benzene layer
customthe residue is purified by chromatography on a silica column

Sources & evidence

ORD record: ord-deb1fb573858420bab6366aab9d0eca8
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04661512

Reaction notes

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