L-Threonine → N-[5-(3-hexadecanoyloxyoctadecanoyl)aminovaleryl]-L-threonine

HRID 1903544Notes

Reaction equation

HRID 1903544 reaction equation
[C:1]([O:18][CH:19]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=O)=[O:22])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[NH2:46][C@H:47]([C:51]([OH:53])=[O:52])[C@@H:48]([CH3:50])[OH:49]>>[C:1]([O:18][CH:19]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([NH:46][C@H:47]([C:51]([OH:53])=[O:52])[C@@H:48]([CH3:50])[OH:49])=[O:30])=[O:22])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 6288L-ThreonineHCID 133718635-(3-Hexadecanoyloxyoctadecanoyl)aminovaleric acid

Product 1

HCID 54382586N-[5-(3-hexadecanoyloxyoctadecanoyl)aminovaleryl]-L-threonineYield 88.4%

Procedure

Starting from 5-(3-hexadecanoyloxyoctadecanoyl)aminovaleric acid (1.27 g) and L-threonine (950 mg), N-[5-(3-hexadecanoyloxyoctadecanoyl)aminovaleryl]-L-threonine (1.3 g) was obtained as crystals according to a similar manner to that of Example 6.

Sources & evidence

ORD record
ord-bb73e8b60f014031b87578fc115ddd2b
Source dataset
uspto-grants-1984_03
Patent number
US04436726

Reaction notes

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