3,4-dihydro-2H-pyran → (2R)-2-[(tert-butoxycarbonyl)amino]-3-(tetrahydro-2H-pyran-2-yloxy)propanoic acid

HRID 2093016Notes

Reaction equation

HRID 2093016 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][OH:14])[C:10]([OH:12])=[O: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.N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][O:14][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:15]1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 637603(R)-2-tert-butoxycarbonylamino-3-hydroxy propionic acid

Product 1

HCID 22882011(2R)-2-[(tert-butoxycarbonyl)amino]-3-(tetrahydro-2H-pyran-2-yloxy)propanoic acidYield 141.1%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2.32 g (0.012 mol) of p-toluensulfonic acid and 0.95 g (0.012 mol) of pyridine in 250 mL of dichloromethane, 25.0 g (0.12 mol) of Intermediate 1 was added. Then, 24.22 g (0.29 mol) of dihydropyran was added dropwise and the resulting mixture was stirred overnight at room temperature. The solvent was removed under vacuum and the residue was redissolved in ethyl acetate (350 mL). The organic phase was washed with water (2×250 mL) and dried over sodium sulphate. The solvent was evaporated under vacuum and 49.00 g of a pale yellow oil was obtained. The oil was not purified and used directly in the following step.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was redissolved in ethyl acetate (350 mL)
  3. washThe organic phase was washed with water (2×250 mL)
  4. dry with materialdried over sodium sulphate
  5. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-a0e7f6b6fa8f4e36a6fe86c8e27945b2
Source dataset
uspto-grants-2013_05
Patent number
US08440861B2

Reaction notes

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