3,4-dihydro-2H-pyran → HCID 22882010, compound

HRID 861918Notes

Reaction equation

HRID 861918 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1>ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][O:11][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 22882010HCID 22882010, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolvent

Procedure

7.65 g of N-t-butoxycarbonyl-L-serine and 3.88 g of 3,4-dihydro-2H-pyrane were dissolved in 60 ml of dichloromethane followed by the addition of 0.47 g of pyridinium p-toluene sulfonate and the solution was stirred for 3 hours at room temperature. After the reaction solution was washed with water and saturated brine, the solvent was distilled off under reduced pressure to obtain 9.90 g of the target compound. Yield: 92%

Workup

  1. washAfter the reaction solution was washed with water and saturated brine
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4e467f1f439d4e0c823d07e2238141d9
Source dataset
uspto-grants-1998_02
Patent number
US05716958

Reaction notes

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