Hydrochloric Acid → HCID 59193310, compound

HRID 1525981Notes

Reaction equation

[C:1]([NH:24][CH2:25][C:26]([NH:28][C:29]1[CH:30]=[CH:31][C:32]([OH:39])=[C:33]([CH:38]=1)[C:34]([O:36]C)=[O:35])=[O:27])(=[O:23])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22].Cl>C1COCC1.[OH-].[Na+]>[C:1]([NH:24][CH2:25][C:26]([NH:28][C:29]1[CH:30]=[CH:31][C:32]([OH:39])=[C:33]([CH:38]=1)[C:34]([OH:36])=[O:35])=[O:27])(=[O:23])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22]

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 5-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoacetamido)-2-hydroxybenzoate (0.9 g, 1.7 mmol) was dissolved in THF (15 mL) and 1N NaOH (8 mL). The reaction was stirred (50° C., 5 h), and then acidified to pH 3 with 2N HCl. The product was extracted with ethyl acetate, and the combined organic extracts were washed with water, brine and dried over MgSO4. The crude material was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to afford 5-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoacetamido)-2-hydroxybenzoic acid (0.40 g) as a yellow solid. Mass calculated for C31H40N2O5=520.66; found: [M+H]+=521.3.

Workup

extractionThe product was extracted with ethyl acetate
washthe combined organic extracts were washed with water, brine
dry with materialdried over MgSO4
customThe crude material was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-4966d9b8efb942669c95cc86ed340d4d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085527B2

Reaction notes

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