Propargylamine → (2S,3R,4R,5R,6R)-6-(acetoxymethyl)-3-(3-(prop-2-yn-1-yl)thioureido)tetrahydro-2H-pyran-2,4,5-triyl triacetate

HRID 1422542Notes

Reaction equation

HRID 1422542 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([N:11]=[C:12]=[S:13])[C@@H:9]([O:14][C:15](=[O:17])[CH3:16])[C@@H:8]([O:18][C:19](=[O:21])[CH3:20])[C@@H:7]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[O:6]1)(=[O:3])[CH3:2].[CH2:27]([NH2:30])[C:28]#[CH:29]>C(Cl)Cl>[C:1]([O:4][C@H:5]1[C@H:10]([NH:11][C:12]([NH:30][CH2:27][C:28]#[CH:29])=[S:13])[C@@H:9]([O:14][C:15](=[O:17])[CH3:16])[C@@H:8]([O:18][C:19](=[O:21])[CH3:20])[C@@H:7]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[O:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 14130736HCID 14130736, compound

Product 1

HCID 86715423(2S,3R,4R,5R,6R)-6-(acetoxymethyl)-3-(3-(prop-2-yn-1-yl)thioureido)tetrahydro-2H-pyran-2,4,5-triyl triacetateYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,3R,4R,5R,6R)-6-(acetoxymethyl)-3-isothiocyanatotetrahydro-2H-pyran-2,4,5-triyl triacetate (1.4 g, 3.6 mmol) in DCM (15 mL) at 0° C., was added propargyl amine (0.345 mL, 5.4 mmol) dropwise. After the addition, reaction mixture was stirred at RT for 1 h. DCM layer was washed with satd. NaHCO3, dried over anhydrous Na2SO4 and concentrated. The crude product (2S,3R,4R,5R,6R)-6-(acetoxymethyl)-3-(3-(prop-2-yn-1-yl)thioureido)tetrahydro-2H-pyran-2,4,5-triyl triacetate (1.59 g, 98%) thus obtained was carried forward without further purification.

Workup

  1. additionAfter the addition, reaction mixture
  2. washDCM layer was washed with satd
  3. dry with materialNaHCO3, dried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2437623c6efb444e8ac53b26c4cf24c4
Source dataset
uspto-grants-2015_01
Patent number
US08927507B2

Reaction notes

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