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2-Chloroethyl methyl ether → (RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2yl)-propionic acid methyl ester

HRID 602755
ノート
印刷プレビュー

反応式

HRID 602755 の反応式
[CH3:1][O:2][C:3](=[O:29])[C:4]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=3)[NH:9][C:8]=2[CH2:7]1)[CH3:5].[H-].[Na+].ClC[CH2:34][O:35][CH3:36]>C1COCC1>[CH3:1][O:2][C:3](=[O:29])[C:4]([S:20]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:22])=[O:21])([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=3)[N:9]([CH2:34][O:35][CH3:36])[C:8]=2[CH2:7]1)[CH3:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 11419051HCID 11419051、化合物

生成物 1

HCID 67267086(RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2yl)-propionic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

350 mg (0.81 mmol) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionic acid methyl ester (from example 3) in 10 mL of THF at 0° C., were treated with 39 mg (0.89 mmol, 1.1 eq) of NaH (55% in oil) portionwise within 30 min. 0.10 mL (1.22 mmol, 1.5 eq) of 1-chloro-2-methoxy-ethane was added and the ice bath removed. After 2 hours, the reaction was quenched by addition of aqueous NH4Cl sat., extracted with EtOAc and the organic phases dried over Na2SO4. Evaporation of the solvent afforded (RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2yl)-propionic acid methyl ester as yellow solid, MS: 493 (MNH4′). The crude material was used in the next step without further purification.

後処理

  1. customthe ice bath removed
  2. customthe reaction was quenched by addition of aqueous NH4Cl sat.
  3. extractionextracted with EtOAc
  4. dry with materialthe organic phases dried over Na2SO4
  5. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-41f47a1717b8438d9816bfbcadf2a372
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07906546B2

反応ノート

読み込み中…

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