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

反応式

HRID 931490 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
35 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d596fa59e9a7434aa2dd98fe6cad7e83
出典データセット
uspto-grants-2016_03
特許番号
US09296732B2

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