Pyridine → Benzyl-5-(N-FMOC-L-valyloxy)-4-stearoyloxy-2-pentenoate

HRID 489065Notes

Reaction equation

HRID 489065 reaction equation
[CH2:1]([O:8][C:9](=[O:40])[CH:10]=[CH:11][CH:12]([OH:39])[CH2:13][O:14][C:15](=[O:38])[C@H:16]([CH:35]([CH3:37])[CH3:36])[NH:17][C:18]([O:20][CH2:21][CH:22]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:47](Cl)(=[O:65])[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64].C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([O:8][C:9](=[O:40])[CH:10]=[CH:11][CH:12]([O:39][C:47](=[O:65])[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[CH2:13][O:14][C:15](=[O:38])[C@H:16]([CH:35]([CH3:37])[CH3:36])[NH:17][C:18]([O:20][CH2:21][CH:22]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8212Stearoyl chlorideHCID 516892Sodium BicarbonateHCID 54039988Benzyl 5-(N-FMOC-L-valyloxy)-4-hydroxy-2-pentenoate

Product 1

HCID 53974693Benzyl-5-(N-FMOC-L-valyloxy)-4-stearoyloxy-2-pentenoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzyl-5-(N-FMOC-L-valyloxy)-4-hydroxy-2-pentenoate (6.5 g, 12 mmol) and pyridine (2.0 g, 25 mmole) in 100 ml dichloromethane at 10° C. was added dropwise a solution of stearoylchloride (4.55 g, 15 mmol) in 25 ml dichloromethane. The mixture was stirred overnight. 100 ml of 5% sodium hydrogencarbonate solution was added and the mixture was stirred for 30 minutes. The organic phase was seperated and the water phase was extracted two times with dichloromethane. The combined organic phases were dried with sodium sulfate and concentrated in vacuo. The product was isolated by silica gel column chromatography Yield: 7.8 g=80%

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. customThe organic phase was seperated
  3. extractionthe water phase was extracted two times with dichloromethane
  4. dry with materialThe combined organic phases were dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe product was isolated by silica gel column chromatography Yield: 7.8 g=80%

Sources & evidence

ORD record
ord-19e81bfb599546b39faf657550c72823
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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