Dicyclohexylcarbodiimide → Fmoc-Gly-OPfp

HRID 393893

반응식

HRID 393893 반응식
[NH:1]([C:6]([O:8][CH2:9][CH:10]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7])[CH2:2][C:3]([OH:5])=[O:4].O[C:24]1[C:33]([F:34])=[C:31]([F:32])[C:29]([F:30])=[C:27]([F:28])[C:25]=1[F:26].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:1]([C:6]([O:8][CH2:9][CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]2[C:22]1=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:7])[CH2:2][C:3]([O:5][C:24]1[C:25]([F:26])=[C:27]([F:28])[C:29]([F:30])=[C:31]([F:32])[C:33]=1[F:34])=[O:4]

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 93124Fmoc-Gly-OH

생성물 1

HCID 2733282Fmoc-Gly-OPfp

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of Fmoc-Gly-OH (891 mg, 3.0 mmol) and PfpOH(754 mg, 4.5 mmol) in DMF (12 mL) was added DCC (845 mg, 4.5 mmol) at 0° C. for 30 min and then room temperature for 15 h. The reaction mixture was filterd to remove DCUrea and the flitrate was evaporated in vacuo to give the crude Fmoc-Gly-OPfp. To a solution of Fmoc-Gly-OPfp and BocPNA-OH (436 mg, 2.0 mmol) in DMF (16 mL) was added diisoprppylethylamine (445 il, 2.6 mmol) and the reaction mixture was stirred at room temperature for 15 h. The reaction mixture was evaporated in vacuo and the residue was flush-chromatographed (0-50% MeOH/CH2Cl2) to give Fmoc-Gly-BocPNA-OH (121 mg, 12%). 1H NMR (DMSO-d6) δ 7.88 (d, J=7.0 Hz, 2H), 7.72 (d, J=7.0 Hz, 2H), 7.62 (brt) and 7.56 (brt) (1H), 7.41 (t, J=7.0 Hz, 2H), 7.33 (t, J=7.0 Hz, 2H), 7.18 (m, 2H), 6.85 (brt) and 6.79 (brt) (1H), 4.35-4.15 (m, 3H), 4.05-3.85 (m, 3H), 3.77 (m, 1H), 3.40-3.25 (m, 2H), 3.10 (m) and 3.03 (s) (2H), 1.37 (brs, 9H); 13C NMR (DMSO-d6) δ 172.2 (d), 169.10 (d), 156.34 (d), 155.58 (d), 143.83, 140.66, 127.58, 127.04, 125.24, 120.04, 77.77 (d), 65.71, 47.34 (d), 46.72, 46.65 (d), 29.23 (d), 28.14 (d); FABMS m/z 498 [(M+H)+].

후처리

  1. customto remove DCUrea
  2. customthe flitrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-c4cc8c272eb84cc2b48907990a8bad74
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809190B2

연결된 노트

불러오는 중…