Methanol → HCID 70232834, compound

HRID 1978060Notes

Reaction equation

HRID 1978060 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:21]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:22]([NH:24][N:25]([S:32]([CH3:35])(=[O:34])=[O:33])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[CH2:9][N:10]1C(=O)C2=CC=CC=C2C1=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN.[CH3:43]O>>[NH2:10][CH2:9][C@@H:8]([C@@H:21]([CH2:36][C:37]([CH3:38])([CH3:43])[CH3:39])[C:22]([NH:24][N:25]([S:32]([CH3:35])(=[O:33])=[O:34])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 69944560HCID 69944560, compound

Product 1

HCID 70232834HCID 70232834, compound

Procedure

A solution of 0.705 g of 2(R)-[1(R)-(tert-butoxycarbonyl)-2-phthalimidoethyl]-2′-(methanesulphonyl)-4-methyl-2′-phenylvalerohydrazide in 15 ml of methanol was treated with 0.51 ml of hydrazine hydrate. The mixture was stirred under nitrogen overnight and then evaporated. The residue was stirred with 25 ml of dichloromethane/methanol/acetic acid/water (120:15:3:2). After 2 hours the precipitated solid was removed by filtration and the filtrate was evaporated. The residue was purified by chromatography on Kieselgel 60 using dichlormethane/methanol/acetic acid/water (240:24:3:2) for the elution. Fractions containing the amine product were combined and evaporated, and the residue was dissolved in 30 ml of dichloromethane and washed with three 10 ml portions of saturated sodium hydrogen carbonate solution. After drying over anhydrous magnesium sulphate the solution was evaporated to give 0.42 g of 2(R)-[2-amino-1(R)-(tert-butoxycarbonyl)ethyl]-2′-(methanesulphonyl)-4methyl-4-methyl-2′-phenylvalerohydrazide in the form of a pale yellow foam.

Workup

  1. customevaporated
  2. stirringThe residue was stirred with 25 ml of dichloromethane/methanol/acetic acid/water (120:15:3:2)
  3. customAfter 2 hours the precipitated solid was removed by filtration
  4. customthe filtrate was evaporated
  5. customThe residue was purified by chromatography on Kieselgel 60 using dichlormethane/methanol/acetic acid/water (240:24:3:2) for the elution
  6. additionFractions containing the amine product
  7. customevaporated
  8. dissolutionthe residue was dissolved in 30 ml of dichloromethane
  9. washwashed with three 10 ml portions of saturated sodium hydrogen carbonate solution
  10. dry with materialAfter drying over anhydrous magnesium sulphate the solution
  11. customwas evaporated

Sources & evidence

ORD record
ord-090083d1ebd74635ad84d35d64b1cc59
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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