Sodium Bicarbonate → (3R,4R)-methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylate

HRID 736783Notes

Reaction equation

HRID 736783 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][C:4]1([CH3:13])[C:9]([O:11][CH3:12])=[O:10].[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:2][C@@H:3]2[CH2:8][CH2:7][O:6][CH2:5][C@:4]2([CH3:13])[C:9]([O:11][CH3:12])=[O:10])(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:2][C@@H:3]2[CH2:8][CH2:7][O:6][CH2:5][C@@:4]2([CH3:13])[C:9]([O:11][CH3:12])=[O:10])(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 47383854-(Benzyloxy)benzene-1-sulfonyl chlorideHCID 68817485Methyl 4-amino-3-methyloxane-3-carboxylate hydrochloride

Product 2

HCID 68818813(3R,4R)-methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylateHCID 68819217(3S,4R)-methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude methyl 4-amino-3-methyl-tetrahydro-2H-pyran-3-carboxylate hydrochloride (8.65 mmol), 4-benzyloxy-benzenesulfonyl chloride (1.2 eq), CH2Cl2 (175 mL) and saturated NaHCO3 (90 mL) were combined and stirred at room temperature overnight. The organic phase was then washed with water (100 mL) and brine (100 mL), dried over MgSO4, and concentrated. The residue was purified by chromatography with 20-35% ethyl acetate/hexane to provide two diastereomers, (3R,4R)-methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylate and (3S,4R)-methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylate. MS: (M+H)+=420.0.

Workup

  1. washThe organic phase was then washed with water (100 mL) and brine (100 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography with 20-35% ethyl acetate/hexane

Sources & evidence

ORD record
ord-97dd439fff3d4c14ba25174825765800
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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