L-Threonine → N-[Nalpha-(3-hexadecanoyloxyoctadecanoyl)-Nepsilon-benzyloxycarbonyl-L-lysyl]-L-threonine

HRID 236508Notes

Reaction equation

HRID 236508 reaction equation
[C:1]([O:18][CH:19]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:20][C:21]([NH:23][C@H:24]([C:40](O)=[O:41])[CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])=[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].[NH2:58][C@H:59]([C:63]([OH:65])=[O:64])[C@@H:60]([CH3:62])[OH:61]>>[C:1]([O:18][CH:19]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:20][C:21]([NH:23][C@H:24]([C:40]([NH:58][C@H:59]([C:63]([OH:65])=[O:64])[C@@H:60]([CH3:62])[OH:61])=[O:41])[CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])=[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 70533277Nalpha-(3-hexadecanoyloxyoctadecanoyl)-Nepsilon-benzyloxycarbonyl-L-lysine

Product 1

HCID 86741316N-[Nalpha-(3-hexadecanoyloxyoctadecanoyl)-Nepsilon-benzyloxycarbonyl-L-lysyl]-L-threonineYield 79.5%

Procedure

Starting from Nα -(3-hexadecanoyloxyoctadecanoyl)-Nε -benzyloxycarbonyl-L-lysine (2.68 g) prepared by the method of Example 20 (1), and L-threonine (0.95 g), N-[Nα -(3-hexadecanoyloxyoctadecanoyl)-Nε -benzyloxycarbonyl-L-lysyl]-L-threonine (2.4 g) was obtained as crystals according to a similar manner to that of Example 32.

Sources & evidence

ORD record
ord-5c5beb7c7dd342da8c0e8d57a8870e20
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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