Carbon Dioxide → HCID 58909210, 화합물

HRID 1295611노트

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HRID 1295611 반응식
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].[CH3:6][CH2:7][CH2:8]CC.[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].[C:24](=[O:26])=O.C([NH2:34])C1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C>[CH2:2]([NH:34][C:24]([C:13]1[CH:14]=[CH:15][O:11][C:12]=1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:26])[C:1]1[CH:4]=[CH:8][CH:7]=[CH:6][CH:3]=1

참가 물질

10

반응물 8

HCID 280Carbon DioxideHCID 7504BenzylamineHCID 8003PentaneHCID 8471TriethylamineHCID 181649HOAtHCID 317628tert-butyl N-(furan-2-yl)carbamateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 58909210HCID 58909210, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

A solution of tert-butyllithium in pentane (2.40 equiv) is added to a solution of tert-butyl 2-furylcarbamate (prepared by the method of Padwa, et al Org Synth 2000, 78, 2002, 1 equiv) in TEF at −78° C. The reaction mixture is stirred for 45 min, then solid CO2 (excess) is added and the resulting mixture is warmed to 0° C. and stirred for 30 minutes. The reaction mixture is partitioned between aqueous 1 N hydrochloric acid solution and ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated. The residue is purified by flash column chromatography (hexanes initially, grading to 100% ethyl acetate), and the polar fractions are concentrated. A solution of the residue, benzylamine (2 equiv), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1 equiv), 1-hydroxy-7-azabenzotriazole (1 equiv), and triethylamine (2 equiv) in DMF is stirred at 55° C. for 24 h. The reaction mixture is concentrated, and the residue is partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated. The residue is purified by flash column (hexanes initially, grading to 100% ethyl acetate) to give tert-butyl 3-[(benzylamino)carbonyl]-2-furylcarbamate (1-1).

후처리

  1. customprepared by the method of Padwa, et al Org Synth 2000, 78, 2002, 1 equiv) in TEF at −78° C
  2. stirringstirred for 30 minutes
  3. customThe reaction mixture is partitioned between aqueous 1 N hydrochloric acid solution and ethyl acetate
  4. dry with materialThe combined organic layers are dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by flash column chromatography (hexanes initially
  7. concentrationare concentrated
  8. concentrationThe reaction mixture is concentrated
  9. customthe residue is partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
  10. dry with materialThe combined organic layers are dried over sodium sulfate
  11. concentrationconcentrated
  12. customThe residue is purified by flash column (hexanes initially

출처 및 근거

ORD 기록
ord-53dccb2481f64771a0ecccd2c2ba9e56
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244723B2

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