Water → N-{[4-(2,3-Butadienyloxy)phenyl]sulfonyl}valine

HRID 1180544Notes

Reaction equation

HRID 1180544 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15](C)[CH:16]([CH:21]([CH3:23])[CH3:22])[C:17]([O:19]C)=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH:2]=[C:3]=[CH2:4].[OH-].[Li+].O>O1CCCC1.CO>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([NH:15][C@H:16]([C:17]([OH:19])=[O:18])[CH:21]([CH3:23])[CH3:22])(=[O:13])=[O:14])=[CH:10][CH:11]=1)[CH:2]=[C:3]=[CH2:4]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 85826253Methyl 2-[{[4-(2,3-butadienyloxy)phenyl]sulfonyl}(methyl)amino]-3-methylbutanoate

Product 1

HCID 86588656N-{[4-(2,3-Butadienyloxy)phenyl]sulfonyl}valineYield 89.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The procedure of Example 12 was followed using the product from Example 14 (300 mg, 0.85 mmol) and lithium hydroxide (41 mg, 1.7 mmol) in tetrahydrofuran (3 ml), methanol (3 ml), and water (1.5 ml) to give 247 mg (86%) of the product.

Sources & evidence

ORD record
ord-435ccad00add432985b7c0b7596e1216
Source dataset
uspto-grants-2007_10
Patent number
US07282496B2

Reaction notes

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