Fmoc isothiocyanate → N-(4-Ethoxycarbonyl-6-methoxypyridin-2-ylmethyl)-N'-(fluoren-9-ylmethyloxycarbonyl)thiourea

HRID 249733

반응식

HRID 249733 반응식
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([O:14][CH3:15])[N:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31]([N:33]=[C:34]=[S:35])=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:5]1[CH:11]=[C:12]([O:14][CH3:15])[N:13]=[C:3]([CH2:2][NH:1][C:34]([NH:33][C:31]([O:30][CH2:29][CH:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:28]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:32])=[S:35])[CH:4]=1)=[O:7])[CH3:10]

참가 물질

4

반응물 2

HCID 4154759Fmoc isothiocyanateHCID 57791316Ethyl 2-aminomethyl-6-methoxyisonicotinate

생성물 1

HCID 57791304N-(4-Ethoxycarbonyl-6-methoxypyridin-2-ylmethyl)-N'-(fluoren-9-ylmethyloxycarbonyl)thiourea수율 29.5%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

6.67 g (31.7 mmol) of ethyl 2-aminomethyl-6-methoxyisonicotinate (20d) were dissolved in 175 ml of toluene and treated at RT with 8.93 g (281.3 mmol) of fluoren-9-ylmethyloxycarbonyl isothiocyanate. After 15 minutes, the resulting precipitate was filtered off and dried at 50° C., 4.6 g of the title compound being isolated. The filtrate was concentrated, and the residue was taken up in DCM and washed three times with water. The organic phase was dried with MgSO4 and concentrated. The crude product thus obtained was chromatographed on silica gel (heptane/ethyl acetate 90:10→75:25), it being possible to isolate a further 8.1 g of the title compound.

후처리

  1. filtrationthe resulting precipitate was filtered off
  2. customdried at 50° C.

출처 및 근거

ORD 기록
ord-63dc31fe34c04da292513138d3624b13
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863269B2

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