Diisopropylethylamine → (2-Hydroxycarbamoyl-1-(4-methoxybenzene sulfonyl)-2,3,4,7-tetrahydro-1H-azepine-3-yl)-carbamic acid benzyl ester

HRID 1872260Notes

Reaction equation

HRID 1872260 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:18][CH:17]=[CH:16][CH2:15][N:14]([S:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:13]1[C:30](O)=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si]([NH:40][OH:41])(C(C)(C)C)(C)C.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH:12]1[CH2:18][CH:17]=[CH:16][CH2:15][N:14]([S:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:13]1[C:30](=[O:31])[NH:40][OH:41])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 155505273-Benzyloxycarbonylamino-1-(4-methoxy-benzene sulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic AcidHCID 17809443t-Butyldimethylsilylhydroxylamine

Product 1

HCID 54472606(2-Hydroxycarbamoyl-1-(4-methoxybenzene sulfonyl)-2,3,4,7-tetrahydro-1H-azepine-3-yl)-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Benzyloxycarbonylamino-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid (21 mg, 0.043 mmol) is dissolved in dry Dimethylformamide (DMF) and cooled to -20° C. tert-Butyldimethylsilylhydroxyl amine (7 mg, 0.05 mmol), Hunigs Base (9.8 μl, 0.05 mmol) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate (HATU) (18 mg, 0.05 mmol) are added. The reaction solution is stirred for 1 h and then allowed to warm to room temp. The solvent is evaporated. The residue is purified by flash-chromatography, Dichloromethane/Methanol (9:1), to afford the desired hydroxamide: Cal. 476.5, Found (MH)+ 476.

Workup

  1. additionare added
  2. customThe solvent is evaporated
  3. customThe residue is purified by flash-chromatography, Dichloromethane/Methanol (9:1)
  4. customto afford the desired hydroxamide

Sources & evidence

ORD record
ord-1ae1e808c2df42f19b4c68eacb5bf125
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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