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

HRID 1662984노트

반응식

HRID 1662984 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c2c1f11ad7ff42c285a20c71b4c08210
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08034810B2

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