HCID 18653518, compound → HCID 18653516, compound

HRID 1728375Notes

Reaction equation

HRID 1728375 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:34])[C@H:7]([NH:18][C@H:19]([C:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:8][CH2:9][O:10][Si](C(C)(C)C)(C)C)([CH3:4])[CH3:3]>C(O)(=O)C>[CH3:1][C:2]([O:5][C:6](=[O:34])[C@H:7]([NH:18][C@H:19]([C:24]([NH:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:8][CH2:9][OH:10])([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 18653518HCID 18653518, compound

Product 1

HCID 18653516HCID 18653516, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.8 g of 2-(R)-[[3-methyl-1-(S)-[(benzylamino)carbonyl]butyl]amino]-4-[((1,1-dimethylethyl)dimethylsilyl)oxy]-butanoic acid-1,1-dimethylethyl ester, prepared as in Example M, in 300 mL acetic acid was stirred for 24 h at 45° C. and the solvent was removed by evaporation. The residue was dissolved in 300 mL ethyl acetate, washed with 3×100 mL sodium bicarbonate, dried (MgSO4), filtered, and the solvents were removed by evaporation. The residue was purified by silica chromatography using methylene chloride:acetone (2:1) as eluent to give the title compound; 5.9 g.

Workup

  1. customthe solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in 300 mL ethyl acetate
  3. washwashed with 3×100 mL sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvents were removed by evaporation
  7. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-4ac7fdd3eb224e29867a447558d72188
Source dataset
uspto-grants-1994_07
Patent number
US05326760

Reaction notes

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