Methanesulfonamide → HCID 49833751, 화합물

HRID 1614863노트

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HRID 1614863 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 49833751HCID 49833751, 화합물수율 95.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-70d1185ea0d64a428e107a0db793f33a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765676B2

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