Ammonium Chloride → HCID 23047388, compound

HRID 2107052Notes

Reaction equation

C(O[C:4]([C:6]1[N:7]=[CH:8][C:9]2[N:10]([S:30]([C:33]3[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:14]=[CH:13][CH:12]=3)=[O:5])C.[CH3:40][Li].[Cl-].[NH4+]>O1CCCC1>[C:4]([C:6]1[N:7]=[CH:8][C:9]2[N:10]([S:30]([C:33]3[CH:34]=[CH:35][C:36]([CH3:37])=[CH:38][CH:39]=3)(=[O:32])=[O:31])[C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:14]=[CH:13][CH:12]=3)(=[O:5])[CH3:40]

Participants

Conditions

Temperature: -60 °C

Procedure

3.3 g of 5-benzyloxy-4-methoxymethyl-9-tosyl-β-carboline-3-carboxylic acid ethyl ester is suspended in 25 ml of absolute tetrahydrofuran (THF) and cooled to -60° C. under an N2 atmosphere. To this suspension is added dropwise 5.2 ml of a 1.5-molar ethereal methyllithium solution and the mixture is stirred for another 2 hours at -60° C. After heating to room temperature, the reaction mixture is combined with saturated ammonium chloride solution and extracted with ethyl acetate. The crude product is purified by chromatography on silica gel with toluene+ethyl acetate in a ratio of 95:5.

Workup

temperatureAfter heating to room temperature
extractionextracted with ethyl acetate
customThe crude product is purified by chromatography on silica gel with toluene+ethyl acetate in a ratio of 95:5

Sources & evidence

ORD record: ord-e581a163e7284f0b8692e7da98324398
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04933345

Reaction notes

Loading…