1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(4-tert-butyl-3,5-difluorophenoxy)-N-((1R)-1-{3-(hydroxymethyl)-4-[(methylsulfonyl)amino]phenyl}ethyl)acetamide

HRID 230594

반응식

HRID 230594 반응식
Cl.[NH2:2][C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:7]([CH2:16][OH:17])[CH:6]=1)[CH3:4].[C:18]([C:22]1[C:32]([F:33])=[CH:31][C:25]([O:26][CH2:27][C:28](O)=[O:29])=[CH:24][C:23]=1[F:34])([CH3:21])([CH3:20])[CH3:19].CN(C)CCCN=C=NCC>CN(C)C=O.CN(C)C1C=CN=CC=1>[C:18]([C:22]1[C:23]([F:34])=[CH:24][C:25]([O:26][CH2:27][C:28]([NH:2][C@@H:3]([C:5]2[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:7]([CH2:16][OH:17])[CH:6]=2)[CH3:4])=[O:29])=[CH:31][C:32]=1[F:33])([CH3:21])([CH3:19])[CH3:20]

참가 물질

6

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68804307N-[4-[(1R)-1-aminoethyl]-2-(hydroxymethyl)phenyl]methanesulfonamide hydrochlorideHCID 68804332(4-tert-Butyl-3,5-difluorophenoxy)acetic acid

생성물 1

HCID 577629242-(4-tert-butyl-3,5-difluorophenoxy)-N-((1R)-1-{3-(hydroxymethyl)-4-[(methylsulfonyl)amino]phenyl}ethyl)acetamide수율 36.4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-[4-[(1R)-1-aminoethyl]-2-(hydroxymethyl)phenyl]methanesulfonamide hydrochloride (40 mg, 0.14 mmol) in N,N-dimethylformamide (DMF) (2 ml), (4-tert-butyl-3,5-difluorophenoxy)acetic acid (34 mg, 0.14 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (40 mg), and 4-dimethylaminopyridine (DMAP) (0.5 mg, 0.004 mmol) were added. The solution was stirred at room temperature for 16 hours and then partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered, and evaporated. The residue obtained was purified by silica gel column chromatography, eluting with methylene chloride/ethylacetate (1:1), to give 2-(4-tert-butyl-3,5-difluorophenoxy)-N-((1R)-1-{3-(hydroxymethyl)-4-[(methylsulfonyl)amino]phenyl}ethyl)acetamide (24 mg, 36%).

후처리

  1. custompartitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by silica gel column chromatography
  7. washeluting with methylene chloride/ethylacetate (1:1)

출처 및 근거

ORD 기록
ord-5d2e081b29804d5292c06fcfc514c624
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566739B2

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