Potassium Hydroxide → HCID 9939669, 화합물

HRID 1954276노트

반응식

HRID 1954276 반응식
C[O:2][C:3]([C:5]1[C:9]([O:10][CH3:11])=[C:8]([S:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:34]4[C:33]([CH3:35])=[C:32]([CH3:36])[S:31][C:30]=4[C:29]([Br:37])=[C:28]4[C:23]=3[CH:24]=[CH:25][CH:26]=[CH:27]4)=[CH:18][C:17]=2[CH:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)(=[O:14])=[O:13])[S:7][CH:6]=1)=[O:4].[OH-].[K+]>C1COCC1.CO>[Br:37][C:29]1[C:30]2[S:31][C:32]([CH3:36])=[C:33]([CH3:35])[C:34]=2[C:22]([C:19]2[CH:20]=[CH:21][C:16]([O:15][S:12]([C:8]3[S:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:9]=3[O:10][CH3:11])(=[O:14])=[O:13])=[C:17]([CH:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)[CH:18]=2)=[C:23]2[C:28]=1[CH:27]=[CH:26][CH:25]=[CH:24]2

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 54249985HCID 54249985, 화합물

생성물 1

HCID 9939669HCID 9939669, 화합물수율 85%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

At ambient temperature, to a stirred solution of 5-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-4-methoxy-thiophene-3-carboxylic acid methyl ester (0.722 g, 1.05 mmol) in THF:MeOH (3:2, 10 mL) was added 1N KOH (5.26 mL). After 1.5 h, the reaction was quenched with 1N HCl (40 mL) and extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated. Purification on 2% H3PO4 /MeOH treated Biotage KP-Sil, eluting with 25% EtOAc/hexane gave 0.596 g (85%) of the title compound as a white solid, mp >225° C.; 1H NMR (DMSO-d6) δ 1.34-1.39 (m, 2 H), 1.49-1.54 (m, 5 H), 1.62-1.73 (m, 3 H), 1.79-1.83 (m, 1 H), 2.43 (s, 3 H), 3.23 (quintet, 1 H), 3.97 (s, 3 H), 7.24 (dd, 1 H), 7.30 (d, 1 H), 7.34-7.36 (m, 2 H), 7.49 (t, 1 H), 7.64 (t, 1 H), 8.19 (d, 1 H), 8.72 (s, 1 H), 13.34 (br. s, 1 H). IR (KBr) 3400, 2950, 1690, 1375 and 860 cm-1. mass spectrum (-ESI), m/z 669/671 (M-H). Anal. Calcd. for C31H27BrO6S3 : C, 55.44; H, 4.05 N, 0.00. Found: C, 55.25; H, 4.11 N, 0.01.

후처리

  1. customthe reaction was quenched with 1N HCl (40 mL)
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customPurification on 2% H3PO4 /MeOH treated Biotage KP-Sil
  6. washeluting with 25% EtOAc/hexane

출처 및 근거

ORD 기록
ord-0fe03e3810584fe78deff384ef045ac1
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06121271

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