Triethylamine → [(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-aminooxan-2-yl]methyl acetate

HRID 1854236Notes

Reaction equation

HRID 1854236 reaction equation
Cl.[C:2]([O:5][C@H:6]1[C@H:11]([NH2:12])[C@@H:10]([O:13][C:14](=[O:16])[CH3:15])[C@H:9]([O:17][C:18](=[O:20])[CH3:19])[C@@H:8]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[O:7]1)(=[O:4])[CH3:3].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:2]([O:5][C@H:6]1[C@H:11]([NH2:12])[C@@H:10]([O:13][C:14](=[O:16])[CH3:15])[C@H:9]([O:17][C:18](=[O:20])[CH3:19])[C@@H:8]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[O:7]1)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20225910034-20-5HCID 516892Sodium Bicarbonate

Product 1

HCID 202260[(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-aminooxan-2-yl]methyl acetateYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-amino-tetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride (250 mg, 0.65 mmol) in CH2Cl2 (5 mL) was added triethylamine (90 μL, 0.65 mmol). The solution was diluted saturated aqueous NaHCO3 (20 mL), then the resulting mixture was extracted with CH2Cl2 (3×10 mL) and the combined organic extracts were dried (Na2SO4) and concentrated to give presumably (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-amino-tetrahydro-2H-pyran-2,4,5-triyl triacetate (220 mg) which was used without further purification.

Workup

  1. extractionthe resulting mixture was extracted with CH2Cl2 (3×10 mL)
  2. dry with materialthe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-02a4b149729f4d40acc075e4b580b4c1
Source dataset
uspto-grants-2015_02
Patent number
US08962664B2

Reaction notes

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