Triethylamine → HCID 86657585, 화합물

HRID 1040426노트

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HRID 1040426 반응식
[C:1](NC1(C(O)=O)CC1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.CN(C(ON1[N:39]=[N:38][C:33]2[CH:34]=C[CH:36]=[N:37][C:32]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:47]([O:51][C:52](NN)=[O:53])([CH3:50])([CH3:49])[CH3:48].CC1C([O:63]C(C)=O)=CC(C(C)C)=C(OCC[NH+](C)C)C=1.[Cl-]>CN(C=O)C.O>[C:47]([O:51][C:52]([NH:39][NH:38][C:33]1([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:34][CH:32]1[N:37]=[C:36]=[O:63])=[O:53])([CH3:50])([CH3:49])[CH3:48]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 13758ArliteneHCID 70091tert-Butyl carbazateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15686068HCID 15686068, 화합물

생성물 1

HCID 86657585HCID 86657585, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-benzoylamino-cyclopropanecarboxylic acid (5.0 g, 21.3 mmol) in DMF (5 mL) was added Et3N (2.94 mL, 21.3 mmol) and HATU (8.08 g, 21.3 mmol). The reaction mixture was allowed to stir for 10 min then hydrazinecarboxylic acid tert-butyl ester (2.81 g, 21.3 mmol) was added. The reaction was allowed to stir at room temperature overnight. The mixture was diluted with water and extracted with EtOAc (3×50 mL). The combined extracts were washed with saturated NaHCO3, 2N HCl, brine and dried with MgSO4. The mixture was filtered, concentrated in vacuo, and purified by silica gel chromatography (25-100% EtOAc in hexanes) to give the N′-(1-benzyloxy-carbonylamino-cyclopropyl)-hydrazinecarboxylic acid tert-butyl ester (6.2 g, 17.7 mmol) as a white solid, m/z 250.6 [M−101]+.

후처리

  1. stirringto stir at room temperature overnight
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined extracts were washed with saturated NaHCO3, 2N HCl, brine
  4. dry with materialdried with MgSO4
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography (25-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-586980b88d01402ea2efb0e4950b4ec7
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552205B2

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