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

HRID 931490

반응식

HRID 931490 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].C(=O)([O-])[O-].[Cs+].[Cs+].I[C@H:26]1[CH2:30][CH2:29][C@H:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:27]1>CN(C)C=O>[C:34]([O:33][C:32]([NH:31][C@H:28]1[CH2:29][CH2:30][C@@H:26]([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])[CH2:27]1)=[O:38])([CH3:37])([CH3:35])[CH3:36]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 86709134Methyl 4-[5-methyl-4-(sulfanylmethyl)-1,3-oxazol-2-yl]benzoateHCID 86709136tert-butyl N-[(1S,3S)-3-iodocyclopentyl]carbamate

생성물 1

HCID 86709137methyl 4-[4-([[(1R,3S)-3-[[(tert-butoxy)carbonyl]amino]cyclopentyl]sulfanyl]methyl)-5-methyl-1,3-oxazol-2-yl]benzoate수율 91.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
35 °C

실험 절차

To a solution of methyl 4-[5-methyl-4-(sulfanylmethyl)-1,3-oxazol-2-yl]benzoate (870 mg, 3.30 mmol, 1.00 equiv) in N,N-dimethylformamide (20 mL) maintained under an atmosphere of nitrogen at 35° C. was added cesium carbonate (2.5 g, 7.65 mmol, 2.32 equiv). After stirring at 35° C. for 20 min, tert-butyl N-[(1S,3S)-3-iodocyclopentyl]carbamate (1.25 g, 4.02 mmol, 1.22 equiv) was then added. The resulting solution was allowed to stir for 50 min at 35° C. under nitrogen after which the product was precipitated by the addition of 50 mL water. The solid was collected by filtration, washed with water then dried in a vacuum oven to give 1.35 g (91%) of methyl 4-[4-([[(1R,3S)-3-[[(tert-butoxy)carbonyl]amino]cyclopentyl]sulfanyl]methyl)-5-methyl-1,3-oxazol-2-yl]benzoate as a white solid.

후처리

  1. stirringto stir for 50 min at 35° C. under nitrogen after which the product
  2. customwas precipitated by the addition of 50 mL water
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customthen dried in a vacuum oven

출처 및 근거

ORD 기록
ord-d596fa59e9a7434aa2dd98fe6cad7e83
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296732B2

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