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

HRID 2194648Notes

Reaction equation

HRID 2194648 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 sated 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. additionThe solution was diluted
  2. extractionthe resulting mixture was extracted with CH2Cl2 (3×10 mL)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e553d3cc8a5a4f659335dd9521e045bd
Source dataset
uspto-grants-2012_12
Patent number
US08334310B2

Reaction notes

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