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

HRID 1662984Notes

Reaction equation

HRID 1662984 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-c2c1f11ad7ff42c285a20c71b4c08210
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

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