L-Alanine → N-Oleoyl Alanine

HRID 1429311Notes

Reaction equation

[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:21][C@H:22]([C:24]([OH:26])=[O:25])[CH3:23]>>[C:1]([NH:21][C@H:22]([C:24]([OH:26])=[O:25])[CH3:23])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

Reactant 2

HCID 5950L-Alanine

HCID 445639Oleic Acid

Product 1

HCID 44423663N-Oleoyl Alanine

Procedure

Prepared as described above in steps 2-4 using oleic acid and L-alanine. (400 MHz, MeOH-d4) δ 0.92 (t, J=5.9 Hz, 3H), 1.27-1.41 (m, 23H), 1.58-1.67 (m, 2H), 2.05 (q, J=5.9 & 12.7 Hz, 4H), 2.23 (t, J=7.8 Hz, 2H), 4.24 (q, J=6.8 & 14.2 Hz, 1H), 5.36 (t, J=4.9 Hz, 2H).

Workup

customPrepared

Sources & evidence

ORD record: ord-58fcdd51291c488f84974e244e301f69
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940665B2

Reaction notes

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