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

HRID 25703

Reaktionsgleichung

Reaktionsgleichung von HRID 25703
[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:21])[C@H:14]([NH2:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:4]1.CN([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27]N=1)C.[CH2:31]([O:38][C:39]([O:41]N1C(=O)CCC1=O)=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N(CC)CC)C.[C:56]([O:59][CH2:60][CH3:61])(=[O:58])C>C(Cl)Cl>[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:21][C:39]([O:38][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:41])[C@@H:14]([NH:20][C:56]([O:59][CH2:60][C:61]2[CH:25]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:58])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:4]1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 218852-DimethylaminopyridineHCID 83172Benzyl succinimido carbonateHCID 86759605Ethyl (2S,3R)-3-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-amino-3-hydroxypropanoate

Produkt 1

HCID 86587935ethyl (2R,3R)-3-[(3aR,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-{[(benzyloxy)carbonyl]amino}-3-{[(benzyloxy)carbonyl]oxy}propanoateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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-amino-3-hydroxypropanoate (5 g, 16.376 mmole, obtained from Reference Example 38), dimethylaminopyridine (195 mg, 1.6 mmole) and N-(benzyloxy)carbonyloxy succinimid (8.2 g, 32.75 mmole) in anhydrous methylene chloride (100 ml) was cooled at 0° C. under argon. Triethylamine (5.1 ml, 36.3 mmole) was introduced to this solution. The resulting mixture was warmed to room temperature and stirred for 15 hours under argon. The mixture was diluted with 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=97:2.5:0.5), to give ethyl (2R,3R)-3-[(3aR,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-{[(benzyloxy)carbonyl]amino}-3-{[(benzyloxy)carbonyl]oxy}propanoate as a white solid (8.36 g, 89%).

Aufarbeitung

  1. washThe organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (silica gel, methylene chloride:ether:methanol=97:2.5:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-263e99c2086d410a8baa6bd60b7a126b
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858591B2

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