HCID 59145551, compound → HCID 59145581, compound

HRID 919111Notes

Reaction equation

HRID 919111 reaction equation
[CH:1]1([C@H:7]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([NH:28][O:29][CH:30]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH3:31])=[O:27])=[CH:20][CH:19]=2)[C:8]([O:10]C2CCCC2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO>[CH:1]1([C@H:7]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([NH:28][O:29][CH:30]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH3:31])=[O:27])=[CH:20][CH:19]=2)[C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 59145551HCID 59145551, compound

Product 1

HCID 59145581HCID 59145581, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

1N NaOHaq (3 mL) was charged to a solution of cyclopentyl (2S)-cyclohexyl[(4-{(1E)-3-[(1-isobutoxyethoxy)amino]-3-oxoprop-1-en-1-yl}benzyl)amino]acetate (prepared as described in Example 14—0.3 g, 0.6 mmol) in MeOH (5 mL) and stirred at 45° C. for 4 days. The MeOH was removed in vacuo and the residue washed with EtOAc (10 mL). The aqueous phase was acidified to pH ˜2 with saturated citric acid solution, extracted with EtOAc (2×10 mL) and the organic phase dried (MgSO4) and concentrated in vacuo to afford the product as a yellow oil (0.14 g, 53%). m/z=433 [M+H]+.

Workup

  1. customThe MeOH was removed in vacuo
  2. washthe residue washed with EtOAc (10 mL)
  3. extractionextracted with EtOAc (2×10 mL)
  4. dry with materialthe organic phase dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb76c4ed74ac4dd78f009e566b413f2e
Source dataset
uspto-grants-2016_03
Patent number
US09273003B2

Reaction notes

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