Hydrochloric Acid → methyl(E)-2-[[2-[2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleryl]hydrazino]sulphonamido]acetic acid

HRID 651827Notes

Reaction equation

HRID 651827 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:19]([NH:21][NH:22][S:23]([NH:26][CH2:27][C:28]([O:30]C)=[O:29])(=[O:25])=[O:24])=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl.O1CCC[CH2:41]1>CO.O>[CH3:41][CH:27]([NH:26][S:23]([NH:22][NH:21][C:19](=[O:20])[C@@H:18]([C@@H:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:32][CH:33]([CH3:34])[CH3:35])(=[O:24])=[O:25])[C:28]([OH:30])=[O:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrate2×HCID 20681577methyl(E)-2-[[2-[2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleryl]hydrazino]sulphonamido]acetate

Product 1

HCID 20681578methyl(E)-2-[[2-[2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleryl]hydrazino]sulphonamido]acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.431 g of methyl(E)-2-[[2-[2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleryl]hydrazino]sulphonamido]acetate in 10 ml of tetrahydrofuran and 5 ml of methanol was treated with 0.040 g of lithium hydroxide monohydrate and the mixture was left to stir overnight. A further 0.020 g of lithium hydroxide monohydrate was added and stirring continued for 4 hours. The mixture was then diluted with water, acidified using 2M aqueous hydrogen chloride, and extracted with ethyl acetate. The ethyl acetate fraction was dried over anhydrous magnesium sulphate and evaporated to give 0.462 g of methyl(E)-2-[[2-[2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleryl]hydrazino]sulphonamido]acetic acid as an oil.

Workup

  1. waitthe mixture was left
  2. stirringstirring
  3. waitcontinued for 4 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate fraction was dried over anhydrous magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-09f0a27974ab4e288ea27eb2f25c3d68
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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