Pyridine → HCID 23387560, compound

HRID 489067Notes

Reaction equation

HRID 489067 reaction equation
[C:1]([NH:18][C@H:19]([C:23]([O:25][CH2:26][CH:27]([OH:38])[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])=[O:24])[CH:20]([CH3:22])[CH3:21])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].N1C=CC=CC=1.[C:45](Cl)(=[O:63])[CH2:46][CH2:47][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][CH3:62].C(=O)([O-])O.[Na+]>ClCCl>[C:1]([NH:18][C@H:19]([C:23]([O:25][CH2:26][CH:27]([O:38][C:45](=[O:63])[CH2:46][CH2:47][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][CH3:62])[C:28]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:29])=[O:24])[CH:20]([CH3:22])[CH3:21])([O:3][CH2:4][CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8212Stearoyl chlorideHCID 516892Sodium BicarbonateHCID 23387559HCID 23387559, compound

Product 1

HCID 23387560HCID 23387560, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of benzyl 3-(N-FMOC-L-valyloxy)-2-hydroxypropionate (4.6 g 8.89 mmole) and pyridine (1.41 g, 17.8 mmole) in 80 ml dichloromethane was added dropwise a solution of stearoylchloride (3.64 g, 12 mmole) in 20 ml dichloromethane and the mixture was stirred overnight at room temperature. 100 ml of 5% sodium hydrogencarbonate solution was added and the mixture 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 chromatography. Yield: 6.1 g=87%

Workup

  1. stirringthe mixture 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 chromatography

Sources & evidence

ORD record
ord-c809f5a12b8c4a22b057fedc36bee19f
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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