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Acetic Acid → 5-(1-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-3-methyl-thiophene-2-sulfonic acid acetyl-amide

HRID 1819949
ノート
印刷プレビュー

反応式

HRID 1819949 の反応式
[C:1]([Si:5]([CH3:37])([CH3:36])[O:6][CH:7]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:21]2[S:25][C:24]([S:26]([NH2:29])(=[O:28])=[O:27])=[C:23]([CH3:30])[CH:22]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][C:11]=1[CH3:31])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.[C:49](O)(=[O:51])[CH3:50]>CN(C1C=CN=CC=1)C.ClCCl>[C:49]([NH:29][S:26]([C:24]1[S:25][C:21]([C:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH:7]([O:6][Si:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:36])[CH3:37])[C:32]([CH3:35])([CH3:34])[CH3:33])=[C:11]([CH3:31])[CH:12]=2)([CH2:17][CH3:18])[CH2:19][CH3:20])=[CH:22][C:23]=1[CH3:30])(=[O:28])=[O:27])(=[O:51])[CH3:50]
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 176Acetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 578901405-(1-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl)-1-ethyl-propyl)-3-methyl-thiophene-2-sulfonic acid amide

生成物 1

HCID 578902375-(1-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-3-methyl-thiophene-2-sulfonic acid acetyl-amide収率 98.4%

試薬・触媒・溶媒

2
HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 5-(1-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-3-methyl-thiophene-2-sulfonic acid amide (227 mg, 0.4 mmol), EDCI (92 mg, 0.48 mmol), acetic acid (27 μL, 0.48 mmol) and DMAP (50 mg) in dichloromethane (10 ml) is stirred at RT overnight. The reaction is diluted with dichloromethane and washed with 1N HCl. The organic phase is concentrated and chromatographed (Hex to 20% EtOAc/Hex) to give the title compound (240 mg, 98%). 1H NMR (CDC3) δ 7.99 (s, 1H), 7.02 (d 1H, J=8.8 Hz), 6.96 (s, 1H), 6.69 (d, 1H, J=8.8 Hz), 6.59 (s, 1H), 3.98 (dd, 1H, J=3.4, 9.8 Hz), 3.85 (dd, 1H, J=5.8, 9.8 Hz), 3.67 (dd, 1H, J=3.4, 5.8 Hz), 2.43 (s, 3H), 2.20 (s, 3H), 2.13 9s, 3H), 2.06 (q, 4H), 0.96 (s, 9H), 0.89 (s, 9H), 0.70 (t, 6H), 0.11 (s, 3H), 0.05 (s, 3H);

後処理

  1. washwashed with 1N HCl
  2. concentrationThe organic phase is concentrated
  3. customchromatographed (Hex to 20% EtOAc/Hex)

出典と根拠

ORDレコード
ord-04546fae9883444e96b752c055bb3713
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07601850B2

反応ノート

読み込み中…

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