Pyridine → 1-O-(N-trityl-L-valyl)-2-allyl-3-stearoyl-1,3-propandiol

HRID 489060Notes

Reaction equation

HRID 489060 reaction equation
[C:1]([NH:20][C@H:21]([C:25]([O:27][CH2:28][CH:29]([CH2:32][CH:33]=[CH2:34])[CH2:30][OH:31])=[O:26])[CH:22]([CH3:24])[CH3:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:41](Cl)(=[O:59])[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][CH2:56][CH2:57][CH3:58]>ClCCl>[C:1]([NH:20][C@H:21]([C:25]([O:27][CH2:28][CH:29]([CH2:32][CH:33]=[CH2:34])[CH:30]([C:41](=[O:59])[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][CH2:56][CH2:57][CH3:58])[OH:31])=[O:26])[CH:22]([CH3:24])[CH3:23])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8212Stearoyl chlorideHCID 23387487HCID 23387487, compound

Product 1

HCID 233874881-O-(N-trityl-L-valyl)-2-allyl-3-stearoyl-1,3-propandiol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-O-(N-trityl-L-valyl)-2-allyl-1,3-propandiol (1.83 g, 4 mmol) in dichloromethane (40 ml) and pyridine (3.2 ml, 40 mmol) at 0° C. was added dropwise stearoyl chloride (3.62 g, 12 mmol) in dichloromethane. The solution was warmed up to room temperature, and kept for 3 hr. It was then washed with sodium hydrogen carbonate aqueous solution and dried. The product was isolated by silica gel column chromatography. 1.9 g

Workup

  1. washIt was then washed with sodium hydrogen carbonate aqueous solution
  2. customdried
  3. customThe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-a2b95c643cac4b3a8e88bf1b283637f8
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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