Potassium Carbonate → Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}-L-glutamate

HRID 591284노트

반응식

HRID 591284 반응식
[F:1][CH2:2][CH2:3]I.C(=O)([O-])[O-].[K+].[K+].[C:11]([O:15][C:16]([NH:18][C@H:19]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:20][C@H:21]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][N:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:17])([CH3:14])([CH3:13])[CH3:12]>CN(C)C=O>[C:11]([O:15][C:16]([NH:18][C@H:19]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:20][C@H:21]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:3][CH2:2][F:1])=[CH:32][N:31]=1)[C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])=[O:17])([CH3:12])([CH3:13])[CH3:14]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 70957058Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-[(5-hydroxypyridin-2-yl)methyl]-L-glutamate

생성물 1

HCID 70674548Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}-L-glutamate수율 81.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 196 mg 1-fluoro-2-iodoethane (1.13 mmol) in N,N-dimethylformamide (25 mL) was subsequently added 363 mg potassium carbonate (2.63 mmol), followed by 350 mg di-tert-butyl (4R)—N-(tert-butoxycarbonyl)-4-[(5-hydroxypyridin-2-yl)methyl]-L-glutamate 0.75 mmol), and the resulting mixture was stirred for 4 h at room temperature. The mixture was than partitioned between water and dichloromethane, and the organic layer was washed with brine, dried over magnesium sulfate, and evaporated. Purification of the crude product by preparative HPLC (method A) gave 313 mg of the target compound (81% yield).

후처리

  1. customthan partitioned between water and dichloromethane
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customPurification of the crude product by preparative HPLC (method A)

출처 및 근거

ORD 기록
ord-d90f8d72f99041f787ac760f5765461a
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238631B2

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