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1-Hydroxybenzotriazole → 2-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]-N-methoxy-N-methylpropaneamide

HRID 1881905
ノート
印刷プレビュー

反応式

HRID 1881905 の反応式
Cl.[CH3:2][O:3][NH:4][CH3:5].[Cl:6][C:7]1[CH:8]=[C:9]([CH:17]([CH2:21][C@H:22]2[CH2:42][CH2:41][C:24]3([O:28][C@H:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C@@H:26]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[O:25]3)[CH2:23]2)[C:18]([OH:20])=O)[CH:10]=[CH:11][C:12]=1[S:13]([CH3:16])(=[O:15])=[O:14].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(#N)C.C(OCC)(=O)C.C(N(CC)CC)C>[Cl:6][C:7]1[CH:8]=[C:9]([CH:17]([CH2:21][C@H:22]2[CH2:42][CH2:41][C:24]3([O:28][C@H:27]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C@@H:26]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[O:25]3)[CH2:23]2)[C:18]([N:4]([O:3][CH3:2])[CH3:5])=[O:20])[CH:10]=[CH:11][C:12]=1[S:13]([CH3:16])(=[O:15])=[O:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 593314112-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propanoic acid

生成物 1

HCID 59331587
2-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]-N-methoxy-N-methylpropaneamide
収率 69%

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of N-methoxymethanamine hydrochloride (936 mg) in acetonitrile (40 mL) was neutralized with triethylamine (3.35 mL), and 2-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propanoic acid (4.33 g), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (2.30 g) and 1-hydroxybenzotriazole (612 mg) were added under ice-cooling. The reaction mixture was stirred overnight at room temperature, diluted with ethyl acetate, and washed with water and saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (3.05 g, yield 69%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (3:1, volume ratio).

後処理

  1. additionwere added under ice-
  2. temperaturecooling
  3. washwashed with water and saturated aqueous sodium hydrogen carbonate
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-e36f0a7231014d4eb6cfcaacbed0fd58
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08318746B2

反応ノート

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