Dicyclohexylcarbodiimide → Ethyl cyclopentanecarboxylate

HRID 731283ノート

反応式

HRID 731283 の反応式
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1NCCC(C)C)=[O:5])[CH3:2].CS(NC1C=CC2NC(CC(O)=O)=NS(=O)(=O)C=2C=1)(=O)=O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.ClCCl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 248585392H-1,2,4-Benzothiadiazine-3-acetic acid, 7-[(methylsulfonyl)amino]-, 1,1-dioxideHCID 57671252HCID 57671252、化合物

生成物 1

HCID 79550Ethyl cyclopentanecarboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
25 °C

実験手順

To a solution of cis-2-(3-methylbutylamino)-cyclopentanecarboxylic acid ethyl ester (53.5 mg, 0.237 mmol) in N,N-dimethylformamide (3.0 mL) was added (7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (prepared as described in Example 1j, 157.4 mg, 0.472 mmol) and a 1.0 M solution of N,N′-dicyclohexylcarbodiimide in dichloromethane (0.47 mL, 0.47 mmol). After stirring at 25° C. for 12 h, the mixture was diluted with dichloromethane and the precipitated N,N′-dicyclohexylurea byproduct was removed by filtration. The filtrate was concentrated and dried in vacuo to afford the crude product, cis-2-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-(3-methylbutyl)amino]-cyclopentanecarboxylic acid ethyl ester, which was used in the next step without further purification. LC-MS (ESI) calcd for C23H34N4O7S2 542.19, found 543.2 [M+H+].

後処理

  1. customthe precipitated N,N′-dicyclohexylurea byproduct was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. customdried in vacuo

出典と根拠

ORDレコード
ord-f3d843cb606a46d9b5f9a5b3770c9a7c
出典データセット
uspto-grants-2009_09
特許番号
US07582626B2

反応ノート

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