Trifluoroacetic acid → (6,7-Bis(palmi toyloxy)-4-thiaheptanoyl)glycylglycylglycine

HRID 1720811Notes

Reaction equation

HRID 1720811 reaction equation
C([O:5][C:6](=[O:61])[CH2:7][NH:8][C:9](=[O:60])[CH2:10][NH:11][C:12](=[O:59])[CH2:13][NH:14][C:15](=[O:58])[CH2:16][CH2:17][S:18][CH2:19][CH:20]([O:40][C:41](=[O:57])[CH2:42][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][CH3:56])[CH2:21][O:22][C:23](=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])(C)(C)C.FC(F)(F)C(O)=O>>[C:41]([O:40][CH:20]([CH2:21][O:22][C:23](=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:19][S:18][CH2:17][CH2:16][C:15]([NH:14][CH2:13][C:12]([NH:11][CH2:10][C:9]([NH:8][CH2:7][C:6]([OH:61])=[O:5])=[O:60])=[O:59])=[O:58])(=[O:57])[CH2:42][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][CH3:56]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22418631(6,7-Bis(palmitoyloxy)-4-thiaheptanoyl)glycylglycylglycine t-butyl ester

Product 1

HCID 22418620(6,7-Bis(palmi toyloxy)-4-thiaheptanoyl)glycylglycylglycineYield 86%

Procedure

(6,7-bis(palmitoyloxy)-4-thiaheptanoyl)glycylglycylglycine t-butyl ester as obtained in Example 5 (110 mg) was mixed with trifiuoroacetic acid (5 ml), followed by stirring at room temperature for 1 hour. The mixture was concentrated to yield the title compound (81 mg, yield 86%) as a colorless crystal.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-96b46bfa02ea424c9898eec59b97bcac
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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