(1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentyl methanesulfonate → methyl 4-[4-([[(1S,3S)-3-[[(tert-butoxy)carbonyl]amino]cyclopentyl]sulfanyl]methyl)-5-methyl-1,3-oxazol-2-yl]benzoate

HRID 931488노트

반응식

HRID 931488 반응식
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][SH:18].CS(O[C@@H:24]1[CH2:28][CH2:27][C@H:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25]1)(=O)=O>CN(C)C=O>[C:32]([O:31][C:30]([NH:29][C@H:26]1[CH2:27][CH2:28][C@H:24]([S:18][CH2:17][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=3)[O:6][C:2]=2[CH3:1])[CH2:25]1)=[O:36])([CH3:35])([CH3:33])[CH3:34]

참가 물질

4

반응물 2

HCID 86608906(1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentyl methanesulfonateHCID 86709134Methyl 4-[5-methyl-4-(sulfanylmethyl)-1,3-oxazol-2-yl]benzoate

생성물 1

HCID 86709135methyl 4-[4-([[(1S,3S)-3-[[(tert-butoxy)carbonyl]amino]cyclopentyl]sulfanyl]methyl)-5-methyl-1,3-oxazol-2-yl]benzoate수율 88%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of methyl 4-[5-methyl-4-(sulfanylmethyl)-1,3-oxazol-2-yl]benzoate (920 mg, 3.49 mmol, 1.00 equiv) in N,N-dimethylformamide (20 mL) maintained under an inert atmosphere of nitrogen was added cescium camonate (2.3 g). The mixture was stirred for 20 min then tert-butyl N-[(1S,3R)-3-(methanesulfonyloxy)cyclopentyl]carbamate (1.0 g, 3.58 mmol, 1.02 equiv) was added. The resulting solution was stirred at 35° C. for 50 min then the product was precipitated by the addition of 50 mL water. The precipitate was collected by filtration, washed with water and then dried under vacuum to give 1.37 g (88%) of methyl 4-[4-([[(1S,3S)-3-[[(tert-butoxy)carbonyl]amino]cyclopentyl]sulfanyl]methyl)-5-methyl-1,3-oxazol-2-yl]benzoate as a white solid. LC-MS: (ES, m/z): 447 [M+H]+, 391, 271, 230, 115.

후처리

  1. additionwas added cescium camonate (2.3 g)
  2. stirringThe resulting solution was stirred at 35° C. for 50 min
  3. customthe product was precipitated by the addition of 50 mL water
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-b2f4a2f4329243b7b25dcfc037238497
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296732B2

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