Triethylamine → (3S,4S)-benzyl 3-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)piperidine-1-carboxylate

HRID 69997노트

반응식

HRID 69997 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@@H:14]([OH:15])[CH2:13][CH2:12][N:11]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>ClCCl>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@@H:14]([O:15][S:34]([CH3:33])(=[O:36])=[O:35])[CH2:13][CH2:12][N:11]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58423176Phenylmethyl (3S,4S)-3-(((1,1-dimethylethoxy)carbonyl)amino)-4-hydroxy-1-piperidinecarboxylate

생성물 1

HCID 86669214(3S,4S)-benzyl 3-(tert-butoxycarbonylamino)-4-(methylsulfonyloxy)piperidine-1-carboxylate수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (3S,4S)-benzyl 3-(tert-butoxycarbonylamino)-4-hydroxypiperidine-1-carboxylate in dichloromethane (0.13 M) was added triethylamine (1.5 equiv.) followed by methanesulfonyl chloride (1.3 equiv.). The reaction was allowed to stir at room temperature for 15 h. The solution was then quenched with saturated NaHCO3, extracted with dichloromethane, dried with sodium sulfate, and concentrated to give the crude product in >95% yield. LCMS (m/z): 428.9/328.9 (MH+), LC Rt=3.81 min.

후처리

  1. customThe solution was then quenched with saturated NaHCO3
  2. extractionextracted with dichloromethane
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d10a97d0011f4c4084f4aea7d4eb5451
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822497B2

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