(-)-Asparagine → Ammonium Aspartate

HRID 2417017Notes

Reaction equation

[NH2:1][C@H:2]([C:7]([O-:9])=[O:8])[CH2:3][C:4]([O-:6])=[O:5].[NH2:10][C@H](C(O)=O)CC(=O)N>>[NH2:1][C@H:2]([C:7]([O-:9])=[O:8])[CH2:3][C:4]([O-:6])=[O:5].[NH4+:10].[NH4+:1]

Participants

Reactant 2

HCID 6267(-)-Asparagine

HCID 5460541l-aspartic acid, sodium salt

Product 1

HCID 86590683Ammonium Aspartate

Conditions

Temperature: 180 °C

Procedure

The IR spectrum of the product obtained after heating at 180° C. for three hours showed the peaks associated with polymers of aspartate, e.g. at 1391 (carboxylate), 1533 and 1589 (primary amide doublet), and 3300 cm−1 (carboxylate), as well as signals characteristic of asparagine residues, at 1648 cm−1 and 3072 cm−1 (side chain of the —CONH2 R-group) (3300 s, 3072 m, 1648 s, 1589 s, 1533 s, 1391. s, 1196 w). After heating at 220° C. for 4.5 hours, the imide signal at 1704 cm−1 began to emerge, as a result of ammonium aspartate residues being converted to succinimides (3292 s, 3057 w, 2933 w, 1704 sh, 1651 s, 1585 s, 1392 m, 1290 w, 1197 w). After heating at 220° C. for 10 hours, the imide signal at 1704 cm−1. became prominent (FIG. 6) (3300 s, 1704 s, 1664 m, 1530 s, 1383 m, 1355 m, 1296 w, 1194 m).

Workup

customThe IR spectrum of the product obtained
custom(3300 s, 3072 m, 1648 s, 1589 s, 1533 s, 1391. s, 1196 w)
temperatureAfter heating at 220° C. for 4.5 hours

Sources & evidence

ORD record: ord-93dfca3fa0b34d0c9bdafda20b8ca37a
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825313B2

Reaction notes

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