Methanol → HCID 18727269, compound

HRID 843024Notes

Reaction equation

HRID 843024 reaction equation
C[Si](I)(C)C.[OH:6][NH:7][C:8](=[O:42])[C@H:9]([NH:25][S:26]([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)(=[O:28])=[O:27])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14]C(OCC1C=CC=CC=1)=O.CO>C(#N)C>[OH:6][NH:7][C:8](=[O:42])[C@H:9]([NH:25][S:26]([N:29]1[CH2:30][CH2:31][N:32]([C:35]2[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=2)[CH2:33][CH2:34]1)(=[O:28])=[O:27])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodide2×HCID 18727270HCID 18727270, compound

Product 1

HCID 18727269HCID 18727269, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl iodide (0.026 ml, 0.19 mmol) was added to a solution of N-hydroxy-6-(benzyloxycarbonyl)amino-2-(R)-{[4-(4-chlorophenyl)piperazine-1-sulfonyl]amino}-hexanoamide (103 mg, 0.19 mmol) [prepared as described in Example 17, Step 3] in acetonitrile (2 ml) at 0° C. The reaction mixture was allowed to warm to RT, and additional trimethylsilyl iodide (0.47 mmol, 0.065 ml) was added in 0.5 equiv. portions over 2.5 h. Methanol (1.0 ml) was added and the reaction mixture was concentrated in vacuo. The residue was chromatographed (SiO2, 2%-10% methanol/methylene chloride) to give N-hydroxy-6-amino-2-(R)-{[4-(4-chlorophenyl)piperazine-1-sulfonyl]amino}hexanoamide (43.5%) as tan solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was chromatographed (SiO2, 2%-10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-770be919b1c4480b83cea774da0361df
Source dataset
uspto-grants-2002_04
Patent number
US06376506B1

Reaction notes

Loading…