Triethylamine → HCID 10653629, compound

HRID 1720822Notes

Reaction equation

HRID 1720822 reaction equation
[C:1]([O:18][CH:19]([CH2:27][O:28][C:29](=[O:45])[CH2:30][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][CH3:44])[CH2:20][S:21][CH2:22][CH2:23][C:24]([OH:26])=O)(=[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].Cl.[C:47]([O:51][C:52](=[O:74])[C@H:53]([CH2:65][CH2:66][C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[NH:54][C:55](=[O:64])[C:56]1[CH:61]=[CH:60][C:59]([CH2:62][NH2:63])=[CH:58][CH:57]=1)([CH3:50])([CH3:49])[CH3:48].C(OP(C#N)(=O)OCC)C.C(N(CC)CC)C>CN(C)C=O>[C:47]([O:51][C:52](=[O:74])[C@H:53]([CH2:65][CH2:66][C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[NH:54][C:55](=[O:64])[C:56]1[CH:61]=[CH:60][C:59]([CH2:62][NH:63][C:24](=[O:26])[CH2:23][CH2:22][S:21][CH2:20][CH:19]([O:18][C:1](=[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])[CH2:27][O:28][C:29](=[O:45])[CH2:30][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][CH3:44])=[CH:58][CH:57]=1)([CH3:49])([CH3:50])[CH3:48]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 105562786,7-Bis(palmitoyloxy)-4-thiaheptanoic acidHCID 67768754HCID 67768754, compound

Product 1

HCID 10653629HCID 10653629, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6,7-bis(palmitoyloxy)-4-thiaheptanoic acid as obtained in Reference Example 4 (210 mg), 4-(aminomethyl)benzoyl-glutamic acid di-t-butyl ester hydrochloride (144 mg), diethylphosphorocyanidate (75 mg) and triethylamine (93 mg) in dimethylformamide (10 ml) was stirred at room temperature for 30 minutes. After solvent concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:2) to yield the title compound (328 mg, yield 99%) as a colorless wax-like substance.

Workup

  1. concentrationAfter solvent concentration under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-616155519ee04d019d66c560d1d6add2
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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