Sodium Hydroxide → HCID 13851772, compound

HRID 1285097Notes

Reaction equation

[NH2:1][C@@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[OH-].[Na+].[C:13](Cl)(=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>CC(C)=O>[C:13]([NH:1][C@@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])(=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

Conditions

Temperature: 10 °C

Procedure

A solution of 75.0 g (510 mmol) of D-glutamic acid in one liter of aqueous acetone (50:50) was adjusted to pH 9.0 with 2N sodium hydroxide. The resulting solution was cooled to 10° C. and treated over 45 minutes with 114.2 g (770 mmol) of heptanoyl chloride, maintaining the pH at 9.0 with 2N sodium hydroxide. The reaction was allowed to warm to room temperature for three hours. The acetone was removed under vacuum, and the resulting aqueous solution was acidified with dilute hydrochloric acid and extracted three times with 700 ml portions of ethyl acetate. The extracts were combined, dried over magnesium sulfate, filtered and concentrated. The resulting oil was triturated with hexane to give 109.8 g (83%) of desired product: mp 92°-96° C.; IR (Nujol) 3300, 2700-3250, 1720, 1625 cm-1 ; NMR (D6 -DMSO) delta 4.20 (m, 1H), 2.28 (t, 2H), 2.20 (t, 2H), 1.85-2.05 (m, 1H), 1.65-1.85 (m, 1H), 1.40-1.60 (m, 2H), 1.15-1.30 (m, 6H), 0.75 (t, 3H); [alpha]D =+9.6 (C=1.0, MeOH).

Workup

temperatureto warm to room temperature for three hours
customThe acetone was removed under vacuum
extractionextracted three times with 700 ml portions of ethyl acetate
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe resulting oil was triturated with hexane

Sources & evidence

ORD record: ord-1012cad4412946cab549869cbb29e84f
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04565653

Reaction notes

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