Dicyclohexylcarbodiimide → 4-Tert-butoxycarbonylamino-1-methyl-1h-pyrrole-2-carboxylic acid benzotriazol-1yl ester

HRID 1634589노트

반응식

HRID 1634589 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]([OH:17])=[O:16])[N:12]([CH3:14])[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:18]1[CH:19]=[CH:20][C:21]2[N:26](O)[N:25]=[N:24][C:22]=2[CH:23]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]([O:17][N:24]2[C:22]3[CH:23]=[CH:18][CH:19]=[CH:20][C:21]=3[N:26]=[N:25]2)=[O:16])[N:12]([CH3:14])[CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 27356364-[(tert-Butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid

생성물 1

HCID 27559874-Tert-butoxycarbonylamino-1-methyl-1h-pyrrole-2-carboxylic acid benzotriazol-1yl ester수율 85%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Boc-Py-acid, 4-[(tert-Butoxycarbonyl)amino]-1-methylpyrrole-2-carboxylic acid (31 g, 129 mmol) was dissolved in 500 mL DMF, HOBt (17.4 g, 129 mmol) was added followed by DCC (34 g, 129 mmol). The reaction was stirred for 24 h and then filtered dropwise into a well stirred solution of 5 L of ice water. The precipitate was allowed to sit for 15 min at 0° C. and then collected by filtration. The wet cake was dissolved in 500 mL DCM, and the organic layer added slowly to a stirred solution of cold petroleum ether (4° C.). The mixture was allowed to stand at −20° C. for 4 h and then collected by vacuum filtration and dried in vacuo to provide (39 g, 85% yield) of 1,2,3-Benzotriazol-1-yl 4-[(tert-butoxycarbonyl)-amino]-1-methylpyrrole-2-carboxylate as a finely divided white powder. TLC (7:2 benzene/ethyl acetate v/v) Rf 0.61H NMR (DMSO-d6) δ 9.43 (s, 1H), 8.12 (d, 1H, J=8.4 Hz), 7.80 (d, 1H, J=8.2 Hz), 7.64 (t, 1H, J=7.0 Hz), 7.51 (m, 2H), 7.18 (s, 1H), 3.83 (s, 3H), 1.45 (s, 9H), 13C NMR (DMSO-d6) δ 156.5, 153.3, 143.2, 129.6, 129.2, 125.7, 125.2, 124.6, 120.3, 112.8, 110.3, 109.8, 79.5, 36.8, 28.6.; IR (KBr) 3246, 3095, 2979, 1764, 1711, 1588, 1389, 1365, 1274, 1227, 1160, 1101, 999, 824, 748.; FABMS m/e 358.152 (M+H 358.151 calc. for C17H20N5O4).

후처리

  1. filtrationfiltered dropwise into a well
  2. stirringstirred solution of 5 L of ice water
  3. waitto sit for 15 min at 0° C.
  4. filtrationcollected by filtration
  5. dissolutionThe wet cake was dissolved in 500 mL DCM
  6. additionthe organic layer added slowly to a stirred solution of cold petroleum ether (4° C.)
  7. waitto stand at −20° C. for 4 h
  8. filtrationcollected by vacuum filtration
  9. customdried in vacuo

출처 및 근거

ORD 기록
ord-ee0e3330230545a694dfdfcff6dfa344
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506906B1

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