1-Hydroxybenzotriazole → 2-([4-(4-fluorobutoxy)-benzenesulfonyl](4-methoxy-benzyl)amino)-N-(1-ethoxy-1-methyl ethoxy)acetamide

HRID 1662984ノート

反応式

HRID 1662984 の反応式
[F:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]([CH2:26][C:27]([OH:29])=O)[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[CH:30]1C=CC2N(O)N=NC=2C=1.[CH3:40][O:41][C:42]([O:45][NH2:46])([CH3:44])[CH3:43]>CN(C=O)C.O>[F:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH2:26][C:27]([NH:46][O:45][C:42]([O:41][CH2:40][CH3:30])([CH3:44])[CH3:43])=[O:29])(=[O:15])=[O:14])=[CH:9][CH:8]=1

参加物

6

反応物 3

HCID 757711-HydroxybenzotriazoleHCID 13608208O-(2-Methoxyisopropyl)hydroxylamineHCID 21884797{[4-(4-Fluoro-butoxy)benzenesulfonyl](4-methoxy-benzyl)-amino}-acetic acid

生成物 1

HCID 866244682-([4-(4-fluorobutoxy)-benzenesulfonyl](4-methoxy-benzyl)amino)-N-(1-ethoxy-1-methyl ethoxy)acetamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 0.425 g (1 mmol) of desired ([4-(4-fluorobutoxy)-benzenesulfonyl]-(4-methoxy-benzyl)-amino)-acetic acid and 0.27 g (2 mmol) of HOBT in 4 ml of DMF, a solution of 0.116 g of O-(1-methoxy-1-methyl-ethyl)-hydroxylamine in 1 ml of DMF and 0.23 g of WSCD were successively added at 0-5° C. and the mixture was stirred for 1 h. After stirring for additional 2 h at r.t., the mixture is diluted with H2O and extracted with AcOEt. The combined extracts are dried over MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; AcOEt:n-hexane=1:1) to give 2-([4-(4-fluorobutoxy)-benzenesulfonyl](4-methoxy-benzyl)amino)-N-(1-ethoxy-1-methyl ethoxy)acetamide; NMR (CDCl3): 1.35 (s, 6H), 1.83-2.0 (m, 4H), 3.29 (s, 3H), 3.70 (s, 2H), 3.78 (s, 3H), 4.08-4.11 (m, 2H), 4.32 (s, 2H), 4.47-4.49 (m, 1H), 4.60 (br s, 1H), 6.80-6.90 (m, 2H), 6.95-7.05 (m, 2H), 7.10-7.25 (m, 2H), 7.79 (d, 2H, J=9.06 Hz), 8.46 (br s, 1H).

後処理

  1. stirringAfter stirring for additional 2 h at r.t.
  2. extractionextracted with AcOEt
  3. dry with materialThe combined extracts are dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by column chromatography on silica gel (eluent; AcOEt:n-hexane=1:1)

出典と根拠

ORDレコード
ord-c2c1f11ad7ff42c285a20c71b4c08210
出典データセット
uspto-grants-2011_10
特許番号
US08034810B2

反応ノート

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