Triethylamine → HCID 178451726, 화합물

HRID 350531노트

반응식

HRID 350531 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[C:18]([N:25]1[CH2:32][CH2:31][CH2:30][C@H:26]1[C:27](O)=[O:28])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:11]([O:10][C:8]([C@H:5]1[CH2:6][CH2:7][C@@H:2]([NH:1][C:27]([CH:26]2[CH2:30][CH2:31][CH2:32][N:25]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:28])[CH2:3][CH2:4]1)=[O:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18646006Benzyl (1r,4r)-4-aminocyclohexane-1-carboxylate

생성물 1

HCID 178451726HCID 178451726, 화합물수율 36%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of benzyl 4-aminocyclohexanecarboxylate (900 mg, 3.9 mmol), boc-proline (830 mg, 3.9 mmol), HOBt (521 mg, 3.9 mmol), and triethylamine (1.6 ml, 11.6 mmol) in CH2Cl2 (30.0 ml) was added EDC.HCl (1.1 g, 5.8 mmol) at 0° C. The reaction mixture was stirred at room temperature for 16 hr, and concentrated in vacuo. Water was added to the residue, and extracted with EtOAc. The extract was washed with sat. NaHCO3, 2-M citric acid, and sat. NaHCO3, then dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with n-hexane-EtOAc (6:1, v/v) as eluent to give benzylcis-4-[(1-tert-butoxycarbonyl-2-pyrrolidinyl)carbonylamino]cyclohexanecarboxylate (600 mg, 36%) as an amorphous solid. 1H-NMR (CDCl3) δ 1.44 (s, 9H), 1.50–1.90 (m, 12H), 2.20–2.26 (m, 1H), 3.25–3.50 (m, 2H), 3.80–3.90 (m, 1H), 4.10–4.25 (m, 1H), 5.12 (s, 2H), 7.35–7.36 (m, 5H).

후처리

  1. concentrationconcentrated in vacuo
  2. additionWater was added to the residue
  3. extractionextracted with EtOAc
  4. washThe extract was washed with sat. NaHCO3, 2-M citric acid, and sat. NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with n-hexane-EtOAc (6:1

출처 및 근거

ORD 기록
ord-21e711bb65254de6ba08a552d6d30d61
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179819B2

반응 노트

불러오는 중…