HCID 18653519, compound → HCID 18653517, compound

HRID 1728376Notes

Reaction equation

HRID 1728376 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:29]=[N:30][CH:31]=[CH:32][CH:33]=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.O>[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]=[N: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 18653519HCID 18653519, compound

Product 1

HCID 18653517HCID 18653517, compound

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
45 °C

Procedure

1.18 g of 2-(R)-[[3-methyl-1-(S)-[((pyridin-3-yl-methyl)amino)carbonyl]butyl]amino]-4-[((1,1-dimethylethyl)dimethylsilyl)oxy]-butanoic acid-1,1-dimethylethyl ester, prepared as in Example O, was added to 48 mL of acetic acid:water (9:1) and the mixture was heated to 45° C. and stirred 16 h. The solvents were removed by evaporation and the residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate, dried (MgSO4). The solvent was removed by evaporation and the residue was purified by silica chromatography using acetone:methylene chloride (1:1) as eluents to give the title compound; 0.513 g.

Workup

  1. customThe solvents were removed by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed by evaporation
  6. customthe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-1b95f12f0b5a4588bb2412e04187b0b5
Source dataset
uspto-grants-1994_07
Patent number
US05326760

Reaction notes

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