3,4-dihydro-2H-pyran → HCID 86727235, compound

HRID 336341Notes

Reaction equation

HRID 336341 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C@H:17]([OH:19])[CH3:18])[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:37]1[CH:42]=[CH:41][CH2:40][CH2:39][CH2:38]1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C@H:17]([O:19][CH:38]1[CH2:39][CH2:40][CH2:41][CH2:42][O:37]1)[CH3:18])[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 2733409HCID 2733409, compound

Product 1

HCID 86727235HCID 86727235, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2S,3R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate (5.0 g, 18.72 mmol) in dichloromethane (100 mL), pyridinium p-toluene sulfonate (0.47 g, 1.87 mmol) and 2,3-dihydropyran (2.6 mL, 28.08 mmol) were added at once and the solution was stirred at room temperature for 16 hours. Saturated sodium bicarbonate solution (50 mL) was added to the reaction mixture, the organic layer was separated and the aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic layers were washed with water (50 mL) and brine solution (50 mL) and dried over sodium sulfate.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (2×50 mL)
  3. washThe combined organic layers were washed with water (50 mL) and brine solution (50 mL)
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-518a3142748249e6a491df9915db46f0
Source dataset
uspto-grants-2014_11
Patent number
US08889671B2

Reaction notes

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