Acetic Anhydride → ethyl (2R,3R)-3-[(3aR,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-(acetyloxy)-2-{[(benzyloxy)carbonyl]amino}propanoate

HRID 25705Notes

Reaction equation

HRID 25705 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C@@H:5]([C@H:13]([OH:31])[C@@H:14]([NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:4]1.CN(C1C=CC=CN=1)C.[C:41](OC(=O)C)(=[O:43])[CH3:42]>N1C=CC=CC=1>[CH3:1][O:2][C@H:3]1[C@@H:7]2[O:8][C:9]([CH3:11])([CH3:12])[O:10][C@@H:6]2[C@H:5]([C@H:13]([O:31][C:41](=[O:43])[CH3:42])[C@@H:14]([NH:20][C:21]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:4]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 86587937ethyl (2R,3R)-3-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoate

Product 1

HCID 86587938ethyl (2R,3R)-3-[(3aR,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-(acetyloxy)-2-{[(benzyloxy)carbonyl]amino}propanoateYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of ethyl (2R,3R)-3-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoate (3.1 g, 7.054 mmole, obtained from Reference Example 42) in acetic anhydride (25 ml) and dry pyridine (50 ml) in the presence of dimethylaminopyridine (500 mg) was stirred at room temperature under nitrogen for 15 hours. The solvent was removed in vacuo, and the residue was dissolved in ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (silica gel, methylene chloride:ether:methanol=97:2:1) to give ethyl (2R,3R)-3-[(3aR,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-(acetyloxy)-2-{[(benzyloxy)carbonyl]amino}propanoate (3.4 g, 100%) as a white amorphous solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed (silica gel, methylene chloride:ether:methanol=97:2:1)

Sources & evidence

ORD record
ord-6cb00bd60abd4da98c36003d75d83a16
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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