Cyclopropaneacetic acid → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(2-cyclopropylacetamido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate

HRID 1854234Notes

Reaction equation

HRID 1854234 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].Cl.CN(C)CCCN=C=NCC.[CH:38]1([CH2:41][C:42](O)=[O:43])[CH2:40][CH2:39]1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:2]([O:5][C@H:6]1[C@H:11]([NH:12][C:42](=[O:43])[CH2:41][CH:38]2[CH2:40][CH2:39]2)[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

6

Reactant 3

HCID 138440Cyclopropaneacetic acidHCID 20225910034-20-5HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67205166(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(2-cyclopropylacetamido)-tetrahydro-2H-pyran-2,4,5-triyl triacetateYield 56%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-amino-tetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride (0.500 g, 1.31 mmol) in CH2Cl2 (20 mL) was added 4-(dimethylamino)pyridine (0.478 g, 3.91 mmol), followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.300 g, 1.57 mmol), and 2-cyclopropylacetic acid (0.146 mL, 1.57 mmol). The reaction was stirred for 12 h. Additional CH2Cl2 (80 mL) was added and the organic layer was washed once with saturated aqueous NaHCO3 (10 mL). The organic layer was then dried (MgSO4) and concentrated in vacuo. Flash chromatography of the crude material on silica gel (3:2 EtOAc:hexanes) afforded (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(2-cyclopropylacetamido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate as a white solid (0.256 g, 56% yield).

Workup

  1. washthe organic layer was washed once with saturated aqueous NaHCO3 (10 mL)
  2. dry with materialThe organic layer was then dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c0df66cfa9043f2a62504f10ef3776a
Source dataset
uspto-grants-2015_02
Patent number
US08962664B2

Reaction notes

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