Methanesulfonamide → HCID 49833751、化合物

HRID 1614863ノート

反応式

HRID 1614863 の反応式
[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:17]=[CH:16][C:10]([O:11][CH2:12][C:13](O)=[O:14])=[CH:9][CH:8]=2)[CH2:3]1.CCN=C=NCCCN(C)C.Cl.[CH3:30][S:31]([NH2:34])(=[O:33])=[O:32]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:30][S:31]([NH:34][C:13](=[O:14])[CH2:12][O:11][C:10]1[CH:16]=[CH:17][C:7]([C@@H:4]2[CH2:5][CH2:6][C:2](=[O:1])[CH2:3]2)=[CH:8][CH:9]=1)(=[O:33])=[O:32]

参加物

6

反応物 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 49834134HCID 49834134、化合物

生成物 1

HCID 49833751HCID 49833751、化合物収率 95.7%

試薬・触媒・溶媒 2

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

反応条件

温度
0 °C

実験手順

(R)-[4-(3-Oxo-cyclopentyl)-phenoxy]-acetic acid (preparation 31) (2.5 mmol, 585 mg) was dissolved in DCM (30 mL) and cooled to 0° C. on an icebath. EDCI.HCl (3.75 mmol, 720 mg), methanesulfonamide (2.75 mmol, 261 mg) and DMAP (3.75 mmol, 458 mg) was added and the reaction mixture left an additional 15 min on the ice bath. The ice bath was then removed and the reaction was allowed to warm to r.t. over night. Quenched with citric acid (10% aq.) and extracted with DCM, then dried over Na2SO4 and concentrated in vacuo to yield the title compound (745 mg, 95%). 1H NMR (300 MHz, CDCl3) δ 8.84 (bs, 1H), 7.25-7.19 (m, 2H), 6.95-6.85 (m, 3H), 4.58 (s, 2H), 3.58-3.08 (m, 5H), 2.78-2.58 (m, 1H), 2.58-2.15 (m, 5H), 2.15-1.78 (m, 1H).

後処理

  1. customThe ice bath was then removed
  2. temperatureto warm to r.t. over night
  3. customQuenched with citric acid (10% aq.)
  4. extractionextracted with DCM
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-70d1185ea0d64a428e107a0db793f33a
出典データセット
uspto-grants-2014_07
特許番号
US08765676B2

反応ノート

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