Dimethylformamide → (S)-2-[(4-Benzyloxycarbonylmethoxy-quinoline-2-carbonyl)-amino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester

HRID 1185482노트

반응식

HRID 1185482 반응식
[CH3:1][O:2][C:3](=[O:28])[C@@H:4]([NH:14][C:15]([C:17]1[CH:26]=[C:25]([OH:27])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)=[O:16])[CH2:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:40]([O:47][C:48](=[O:51])[CH2:49]Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O>[CH3:1][O:2][C:3](=[O:28])[C@@H:4]([NH:14][C:15]([C:17]1[CH:26]=[C:25]([O:27][CH2:49][C:48]([O:47][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:51])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)=[O:16])[CH2:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 62576Benzyl bromoacetateHCID 178501467HCID 178501467, 화합물

생성물 1

HCID 68600712(S)-2-[(4-Benzyloxycarbonylmethoxy-quinoline-2-carbonyl)-amino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 6.5 g of (S)-2-[(4-Hydroxy-quinoline-2-carbonyl)-amino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester 50 ml of DMF, 6.5 g of cesium carbonate and 4.2 g of Bromo-acetic acid benzyl ester was added and stirred for 16 h. Then, the reaction mixture was diluted with water and extracted with DCM (3×150 ml). The combined organic phases were dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was used in the next reaction step. Yield: 8.9 g.

후처리

  1. extractionextracted with DCM (3×150 ml)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was used in the next reaction step

출처 및 근거

ORD 기록
ord-7a6bafbf003845d49acb08dafef54bde
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669266B2

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