Potassium Hydroxide → HCID 69072340, compound

HRID 2101218Notes

Reaction equation

HRID 2101218 reaction equation
[OH-].[K+].[C:3]([O:7][C:8](=[O:49])[CH:9]([CH2:34][C:35]1[CH:36]=[N:37][C:38]([NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[CH:39][CH:40]=1)[CH:10]([S:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[C:16]([O:18]CC)=[O:17])([CH3:6])([CH3:5])[CH3:4]>C(O)C.C(OCC)C.O.C1(C)C=CC=CC=1>[C:3]([O:7][C:8](=[O:49])[CH:9]([CH2:34][C:35]1[CH:36]=[N:37][C:38]([NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[CH:39][CH:40]=1)[CH:10]([S:24][CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1)[CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[C:16]([OH:18])=[O:17])([CH3:5])([CH3:6])[CH3:4]

Participants

7

Reactant 2

HCID 14797Potassium HydroxideHCID 69071954HCID 69071954, compound

Product 1

HCID 69072340HCID 69072340, compoundYield 54%

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

KOH (5 mL of a 1M solution in ethanol) was added to a solution of ethyl 3-{5-tert-butoxy-4-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]-5-oxopentyl}benzoate (0.27 g, 0.406 mmol, synthesised according to the procedure for Example 1) in ethanol (2 mL), and the mixture was stirred at room temperature for 2 h and then at 50° C. for 2 h. The reaction mixture was then diluted with diethyl ether and water. The organic phase was extracted with 0.1M aqueous KOH and the combined aqueous phase was acidified (pH 5) using 3M aqueous HCl. The aqueous phase was then extracted with diethyl ether and the organic phase was washed with brine, dried and concentrated. Purification of the residue by reversed-phase HPLC (C-8 column, linear gradient 40%→100% of MeCN in 5% aqueous MeCN containing 0.1 M ammonium acetate) gave a residue that was dissolved in toluene and water and concentrated to give 3-{5-tert-butoxy-4-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]-5-oxopentyl}benzoic acid (0.12 g, 54%).

Workup

  1. customsynthesised
  2. waitat 50° C. for 2 h
  3. extractionThe organic phase was extracted with 0.1M aqueous KOH
  4. extractionThe aqueous phase was then extracted with diethyl ether
  5. washthe organic phase was washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customPurification of the residue by reversed-phase HPLC (C-8 column, linear gradient 40%→100% of MeCN in 5% aqueous MeCN containing 0.1 M ammonium acetate)
  9. customgave a residue that
  10. concentrationwater and concentrated

Sources & evidence

ORD record
ord-4f66de2adbfc4e3c854c1866ceb6f974
Source dataset
uspto-grants-2009_08
Patent number
US07572817B2

Reaction notes

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