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1-Hydroxybenzotriazole → (2R)-1-[3-methoxy-5-(trifluoromethyl)-benzoyl]-2-[4-chloro-3-(tert-butyldimethylsilyloxy)benzyl]-4-benzylpiperazine

HRID 1374998
ノート
印刷プレビュー

反応式

HRID 1374998 の反応式
Cl.CN(C)CCCN=C=NCC.[CH2:13]([N:20]1[CH2:25][CH2:24][NH:23][C@H:22]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH:28]=2)[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:42][O:43][C:44]1[CH:45]=[C:46]([CH:50]=[C:51]([C:53]([F:56])([F:55])[F:54])[CH:52]=1)[C:47](O)=[O:48].ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>ClCCl.O>[CH3:42][O:43][C:44]1[CH:45]=[C:46]([CH:50]=[C:51]([C:53]([F:54])([F:55])[F:56])[CH:52]=1)[C:47]([N:23]1[CH2:24][CH2:25][N:20]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:21][C@H:22]1[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH:28]=1)=[O:48]
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 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 215444673-Methoxy-5-(trifluoromethyl)benzoic acidHCID 54436042(2R)-4-benzyl-2-[4-chloro-3-(tert-butyldimethylsilyloxy)benzyl]piperazine

生成物 1

HCID 57092342
(2R)-1-[3-methoxy-5-(trifluoromethyl)-benzoyl]-2-[4-chloro-3-(tert-butyldimethylsilyloxy)benzyl]-4-benzylpiperazine
収率 77.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.93 g) was added to a mixture of (2R)-4-benzyl-2-[4-chloro-3-(tert-butyldimethylsilyloxy)benzyl]-piperazine (2.90 g) and 3-methoxy-5-(trifluoromethyl)benzoic acid (1.48 g), 1-hydroxybenzotriazole (1.14 g) in dichloromethane (18 ml) at room temperature. After being stirred for 6 hours at the same temperature, the reaction mixture was poured into a mixed solvent of water (25 ml) and dichloromethane (15 ml). The aqueous layer was adjusted to pH 9 with aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (52 g) using a mixed solvent of hexane and ethyl acetate (2:1). The fractions containing the objective compound was collected and evaporated under reduced pressure to give a syrup of (2R)-1-[3-methoxy-5-(trifluoromethyl)-benzoyl]-2-[4-chloro-3-(tert-butyldimethylsilyloxy)benzyl]-4-benzylpiperazine (3.3 g).

後処理

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel (52 g)
  6. additionThe fractions containing the objective compound
  7. customwas collected
  8. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-5d9bd598391b4715a86c035ecbc1d9f1
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07166598B2

反応ノート

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