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

反応式

HRID 25703 の反応式
[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

参加物

7

反応物 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

生成物 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}propanoate収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-263e99c2086d410a8baa6bd60b7a126b
出典データセット
uspto-grants-2005_02
特許番号
US06858591B2

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