Hydrochloric Acid → HCID 20429536, compound
Reaction equation
[C:1](O)(=O)[CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][C:8]#[C:9][CH2:10][C:11]#[C:12][CH2:13][C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]C.S(Cl)(Cl)=[O:25].C[N:29](C)[CH:30]=[O:31].Cl>C(Cl)Cl.CCOCC>[C:30]([NH:29][OH:25])(=[O:31])[CH2:20][CH2:19][CH2:18][C:17]#[C:16][CH2:15][C:14]#[C:13][CH2:12][C:11]#[C:10][CH2:9][C:8]#[C:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]Participants
Procedure
Heneicosa-5,8,11,14-tetraynoic acid (130 mg) was dissolved in methylene chloride (3 ml) and a solution of thionyl chloride (104 mg) and dimethylformamide (5 mg) in methylene chloride (2.6 ml) was added. After 3 hours at 25° C., the solution was evaporated. To the residue was added a solution of hydroxylamine hydrochloride (58 mg) and sodium bicarbonate (70 mg) in water (0.4 ml) and methanol (0.4 ml) to which had been added normal aqueous potassium hydroxide sufficient to obtain a pH of 9. After 10 minutes ether (20 ml) and 1.0N hydrochloric acid (10 ml) were added. The organic solution was dried and evaporated, and the residue was chromatographed on silica gel, eluting with methylene chloride/methanol/ammonium hydroxide, (40/4/0.3;v/v/v) so as to afford the title compound as a solid, m.p.: 85°-88° C.
Workup
- customthe solution was evaporated
- additionTo the residue was added a solution of hydroxylamine hydrochloride (58 mg) and sodium bicarbonate (70 mg) in water (0.4 ml) and methanol (0.4 ml) to which
- additionhad been added normal aqueous potassium hydroxide sufficient
- customto obtain a pH of 9
- customThe organic solution was dried
- customevaporated
- customthe residue was chromatographed on silica gel
- washeluting with methylene chloride/methanol/ammonium hydroxide, (40/4/0.3;v/v/v) so as
Sources & evidence
- ORD record
- ord-2a839eaf191c47aea14b6d4c833f77a1
- Source dataset
- uspto-grants-1985_02
- Patent number
- US04497827
Reaction notes
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