Acetic Acid → ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylaminomethyl]benzoate

HRID 1106790Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:12]=1[CH2:13][NH:14][CH2:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:32](I)[CH3:33].C(O)(=O)C>CN(C=O)C.O>[CH2:3]([O:10][C:11]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:12]=1[CH2:13][N:14]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=1)[CH2:32][CH3:33])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of NaH (1.05 g, 50% dispersion in oil) in DMF (100 ml) at 0° C. was added a solution of ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)aminomethyl]benzoate dropwise. The mixture was stirred at 0° C. for 1 hour, ethyl iodide (3.43 g) added and the mixture stirred at ambient temperature for 18 hours. The mixture was acidified with acetic acid, poured into water (300 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with water (3×100 ml), dried and evaporated. The residue was purified by chromatography eluting with 4% ethyl acetate/CH2Cl2 to give ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylaminomethyl]benzoate (yield 6.61 g).

Workup

stirringthe mixture stirred at ambient temperature for 18 hours
extractionextracted with ethyl acetate (3×100 ml)
washThe combined extracts were washed with water (3×100 ml)
customdried
customevaporated
customThe residue was purified by chromatography
washeluting with 4% ethyl acetate/CH2Cl2

Sources & evidence

ORD record: ord-4c6d1a62b814475aac422e092b232629
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057345

Reaction notes

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