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

反応式

HRID 230594 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-5d2e081b29804d5292c06fcfc514c624
出典データセット
uspto-grants-2009_07
特許番号
US07566739B2

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