Potassium Carbonate → HCID 69763061, compound

HRID 1006097Notes

Reaction equation

HRID 1006097 reaction equation
[C:1]([O:5][C:6](=[O:23])[C@H:7]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[N+:30]([C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[CH3:41])[CH2:36]Cl)([O-:32])=[O:31]>CN(C)C=O>[C:1]([O:5][C:6](=[O:23])[C@H:7]([N:11]([CH2:36][C:35]1[CH:38]=[CH:39][C:40]([CH3:41])=[C:33]([N+:30]([O-:32])=[O:31])[CH:34]=1)[S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5977304-(Chloromethyl)-2-nitrotolueneHCID 10807324N-[(4-methoxyphenyl)sulfonyl]-D-valine tert-butyl ester

Product 1

HCID 69763061HCID 69763061, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2(R)-(4-methoxybenzenesulfonylamino)-3-methylbutyric acid tert-butyl ester (0.15 g, 0.44 mmol) and potassium carbonate (0.32 g, 2.32 mmol) in dry dimethylformamide (15 mL) was added 3-nitro-4-methylbenzyl chloride (81.1 mg. 0.44 mmol). The reaction mixture was stirred overnight and then concentrated on the rotoevaporator. The residue was dissolved in a 1:1 ethyl acetate and brine (50 mL). The organic phase was isolated, dried over magnesium sulfate, and concentrated to give 2(R)-[(3-nitro-4-methylbenzyl)-(4-methoxybenzenesulfonyl)amino]-3-methylbutyric acid tert-butyl ester (0.196 g) as a yellow viscous oil which was converted to 2(R)-[(3-nitro-4-methylbenzyl)-(4-methoxy-benzenesulfonyl)amino]-3-methylbutyric acid by following the procedure described in Example 10, Step 8 below. 2(R)-[(3-nitro-4-methylbenzyl)-(4-methoxybenzenesulfonyl)-amino]-3-methylbutyric acid is then converted to N-hydroxy-2(R)-[(3-nitro-4-methylbenzyl)-(4-methoxybenzenesulfonyl)amino]-3-methylbutyramide by following Example 1, Steps 6 and 7 above.

Workup

  1. concentrationconcentrated on the rotoevaporator
  2. dissolutionThe residue was dissolved in a 1:1 ethyl acetate and brine (50 mL)
  3. customThe organic phase was isolated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f75fc3221c364ab3b7b310df1a4a8c7e
Source dataset
uspto-grants-2004_09
Patent number
US06787559B2

Reaction notes

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