Sodium Azide → (R)-4-((2R,4R,6R)-4-Azido-2-methoxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one

HRID 2251792ノート

反応式

HRID 2251792 の反応式
FC(F)(F)S(O[C@H:7]1[CH2:12][C@@H:11]([CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17])[O:10][C@@:9]([O:33][CH3:34])([C@@H:18]2[CH2:22][S:21][C:20](=[O:23])[N:19]2[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH2:8]1)(=O)=O.[N-:37]=[N+:38]=[N-:39].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N:37]([C@@H:7]1[CH2:12][C@@H:11]([CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17])[O:10][C@:9]([C@@H:18]2[CH2:22][S:21][C:20](=[O:23])[N:19]2[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)([O:33][CH3:34])[CH2:8]1)=[N+:38]=[N-:39]

参加物

5

反応物 2

HCID 33557Sodium AzideHCID 59644094(2R,4S,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-(pent-4-enyl)-tetrahydro-2H-pyran-4-yl Trifluoromethanesulfonate

生成物 1

HCID 59644060(R)-4-((2R,4R,6R)-4-Azido-2-methoxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one収率 82%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of the title compound from Example 22 (1.19 mmol, used directly from the previous reaction) in DMF (12 mL) was treated with sodium azide (400 mg, 6.15 mmol), and the mixture was stirred at room temperature for 22 h. The reaction mixture was diluted with ethyl acetate, washed with satd aq NaHCO3, ice cold 5% aq citric acid, and brine, and the organic phase was dried and concentrated. Chromatography of the residue on silica gel eluting with dichloromethane/ethyl acetate gave the title compound (432 mg, 82%) as an oil.

後処理

  1. washwashed with satd aq NaHCO3, ice cold 5% aq citric acid, and brine
  2. customthe organic phase was dried
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-e4179645ad8b4bafb204a2da11ad0ee5
出典データセット
uspto-grants-2008_01
特許番号
US07320974B2

反応ノート

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