Trifluoroacetic acid → (6,7-Bis(palmitoyloxy),4-thiaheptanoyl)glycylglycine

HRID 1720809Notes

Reaction equation

HRID 1720809 reaction equation
C([O:5][C:6](=[O:57])[CH2:7][NH:8][C:9](=[O:56])[CH2:10][NH:11][C:12](=[O:55])[CH2:13][CH2:14][S:15][CH2:16][CH:17]([O:37][C:38](=[O:54])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH2:18][O:19][C:20](=[O:36])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])(C)(C)C.O1CC1C(O)C.FC(F)(F)C(O)=O>>[C:38]([O:37][CH:17]([CH2:18][O:19][C:20](=[O:36])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:16][S:15][CH2:14][CH2:13][C:12]([NH:11][CH2:10][C:9]([NH:8][CH2:7][C:6]([OH:57])=[O:5])=[O:56])=[O:55])(=[O:54])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 115934311-(Oxiran-2-yl)ethan-1-olHCID 22418588(6,7-Bis(palmitoyloxy)-4-thiaheptanoyl)glycylglycine t-butyl ester

Product 1

HCID 22353662(6,7-Bis(palmitoyloxy),4-thiaheptanoyl)glycylglycineYield 100%

Procedure

To (6,7-bis(palmitoyloxy)-4-thiaheptanoyl)glycylglycine t-butyl ester as obtained in Example 3 (190 mg), trifiuoroacetic acid (2 ml) was added, followed by stirring at room temperature for I hour. The mixture was concentrated to yield the title compound (178 mg, yield 100%) as a colorless crystal.

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-07334b6b527449bfa0c585077a279f1e
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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