Triethylamine → HCID 21326422, compound

HRID 26035

Reaction equation

C(OC([NH:11][C:12]([CH:21]=[CH2:22])([CH2:16][CH2:17][C:18]([OH:20])=O)[C:13]([OH:15])=O)=O)C1C=CC=CC=1.C([N:25]([CH2:28][CH3:29])CC)C.Cl[C:31]([O:33]CC)=[O:32].C[O:37][C:38](=[O:42])[C@H:39]([CH3:41])[NH2:40]>C(Cl)Cl>[NH2:11][C:12]([CH:21]=[CH2:22])([CH2:16][CH2:17][C:18](=[O:20])[NH:25][CH:28]([CH3:29])[C:31]([OH:33])=[O:32])[C:13](=[O:15])[NH:40][CH:39]([CH3:41])[C:38]([OH:37])=[O:42]

Participants

Conditions

Temperature: 25 °C

Procedure

To 2-(benzyloxycarbonyl)amino-2-vinylglutaric acid (305 mg, 1 mM) in methylene chloride (15 ml) is added triethylamine (205 mg, 2 mM) followed by ethyl chloroformate (218 mg, 2 mM). The solution is stirred for one hour at 25° C., then alanine methyl ester (206 mg, 2 mM) in methylene chloride (5 ml) is added. This solution is kept overnight at 25° C., washed with water, dried and evaporated to dryness. The residue is treated with 5 ml of a 40% (w/w) solution of hydrogen bromide in dioxane at 25° C. for 30 minutes. Ether (50 ml) is then added and the precipitate collected. This is then treated with 20 ml of a 1 N sodium hydroxide solution overnight at 25° C., the pH adjusted to 6.5, and applied to an Amberlite 120 H+ resin. Elution with 2 N ammonium hydroxide afforded 5-amino-2,10-dimethyl-4,8-dioxo-5-vinyl-3,9-diazaundecanedioic acid.

Workup

waitThis solution is kept overnight at 25° C.
washwashed with water
customdried
customevaporated to dryness
additionThe residue is treated with 5 ml of a 40% (w/w) solution of hydrogen bromide in dioxane at 25° C. for 30 minutes
additionEther (50 ml) is then added
customthe precipitate collected
additionThis is then treated with 20 ml of a 1 N sodium hydroxide solution overnight at 25° C.
washElution with 2 N ammonium hydroxide

Sources & evidence

ORD record: ord-dbca350db4ff403ca0a0c18ad91427fb
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04147873

Linked notes

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