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Cesium carbonate → (2S,3R,6S)-4-[4-(4-hydroxy-4-methyl-pent-2-ynyloxy)-benzenesulfonyl]-2,6-dimethyl-morpholine-3-carboxylic acid methyl ester

HRID 1935342
ノート
印刷プレビュー

反応式

HRID 1935342 の反応式
[CH3:1][O:2][C:3]([C@H:5]1[C@H:10]([CH3:11])[O:9][C@@H:8]([CH3:12])[CH2:7][N:6]1[S:13]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])=[O:4].I[CH2:24][C:25]#[C:26][C:27]([CH3:30])([OH:29])[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)C>[CH3:1][O:2][C:3]([C@H:5]1[C@H:10]([CH3:11])[O:9][C@@H:8]([CH3:12])[CH2:7][N:6]1[S:13]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:24][C:25]#[C:26][C:27]([OH:29])([CH3:30])[CH3:28])=[CH:20][CH:21]=1)(=[O:15])=[O:14])=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 120166895-Iodo-2-methyl-pent-3-yn-2-olHCID 12016690(2S,3R,6S)-4-(4-Hydroxy-benzenesulfonyl)-2,6-dimethyl-morpholine-3-carboxylic acid methyl ester

生成物 1

HCID 12016682(2S,3R,6S)-4-[4-(4-hydroxy-4-methyl-pent-2-ynyloxy)-benzenesulfonyl]-2,6-dimethyl-morpholine-3-carboxylic acid methyl ester

試薬・触媒・溶媒 2

HCID 3283
Diethyl Ether
溶媒
HCID 6228Dimethylformamide溶媒

実験手順

(2S,3R,6S)-4-(4-Hydroxy-benzenesulfonyl)-2,6-dimethyl-morpholine-3-carboxylic acid methyl ester, (200 mg, 0.607 mmol) (prepared according to the methods described in U.S. patent application Ser. No. 60/096256, filed Aug. 12, 1998) was dissolved in dimethyl formamide (6 mL). 5-Iodo-2-methyl-pent-3-yn-2-ol (272 mg, 1.214 mmol) and cesium carbonate (593 mg, 1.821 mmol) were added and the reaction stirred at room temperature for 4 hours. The reaction was diluted with diethyl ether (100 mL) and washed with water (5 times 10 mL) and brine (30 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo to yield the title compound. The crude material was used directly in the preparation of Example 1 without further purification. 1HNMR (400 MHz, CDCl3): δ=7.70 (d, J=8.9 Hz, 2H), 7.0 (d, J=8.9 Hz, 2H), 4.74 (bs, 2H), 4.50 (q, J=6.6 Hz, 1H), 4.26 (s, 1H), 3.92 (m, 1H), 3.54 (s, 3H), 3.50 (m, 1H), 2.93 (dd, J=12.3 and 11.0 Hz, 1H), 1.48(s, 6H), 1.44 (d, J=5.4 Hz, 3H), 1.01(d, J=6.0, 3H). MS: Calculated for C20H27NO7S (M−OH): 408.15. Found: 408.1.

後処理

  1. washwashed with water (5 times 10 mL) and brine (30 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-75a4b9ea2cdc42348551099dd183f4ae
出典データセット
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06387901B1

反応ノート

読み込み中…

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