1,2-Dichloroethane → (2S,4S)-tert-butyl 4-azido-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate

HRID 1361333노트

반응식

HRID 1361333 반응식
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+:14]=[N-:15])[CH2:10][C@H:9]1[C:16]([OH:18])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[CH2:20][N:21](C(C)C)[CH:22](C)C.CNC.C1COCC1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+:14]=[N-:15])[CH2:10][C@H:9]1[C:16]([N:21]([CH3:22])[CH3:20])=[O:18])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 12094910(2S,4S)-4-azido-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 22320367Dimethylamine tetrahydrofuran

생성물 1

HCID 86636654(2S,4S)-tert-butyl 4-azido-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate수율 479.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (2S,4S)-1-Boc-4-azidopyrrolidine-2-carboxylic acid (9.5 g, 35 mmol) prepared in Step A in DMF (30□) was added dropwise DIPEA (1.15□, 6.70 mmol), and added dropwise 2M dimethylamine-THF solution (26.3 ml, 52.5 mmol), HOBT (7 g, 52.5 mmol) and EDC (10.2 g, 52.5 mmol) in order. The reaction mixture was stirred at rt for 12 h, and concentrated in vacuo. The residue was diluted with EtOAc, and washed with a saturated NaHCO3 aqueous solution, water and 1N HCl. The organic solution was dried over MgSO4, concentrated in vacuo, and the residue was purified by column chromatography (eluent: EtOAc:Hex=1/2) to give the title compound (9.1 g, 93%).

후처리

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed with a saturated NaHCO3 aqueous solution, water and 1N HCl
  4. dry with materialThe organic solution was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by column chromatography (eluent: EtOAc:Hex=1/2)

출처 및 근거

ORD 기록
ord-77ab9ea1557b43738338d434dfc13f9d
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879852B2

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