HCID 58636783, compound → HCID 58636823, compound

HRID 1158950Notes

Reaction equation

HRID 1158950 reaction equation
C([O:8][C:9]1[C:10]([CH3:42])=[N:11][CH:12]=[C:13]([CH2:25][NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([C:39](=[NH:41])[NH2:40])=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)[C:14]=1[CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])C1C=CC=CC=1>CO.[Pd]>[OH-:8].[NH4+:11].[C:39]([C:36]1[CH:37]=[CH:38][C:33]([C:30]2[CH:29]=[CH:28][C:27]([NH:26][CH2:25][C:13]3[C:14]([CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[C:9]([OH:8])[C:10]([CH3:42])=[N:11][CH:12]=3)=[CH:32][CH:31]=2)=[CH:34][CH:35]=1)(=[NH:40])[NH2:41]

Participants

5

Reactant 1

HCID 58636783HCID 58636783, compound

Product 2

HCID 14923Ammonium HydroxideYield 30%HCID 58636823HCID 58636823, compoundYield 191.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

The debenzylation of 6-({3-benzyloxy-5-[(4′-carbamimidoyl-biphenyl-4-ylamino)-methyl]-2-methyl-pyridin-4-ylmethyl}-amino)-hexanoic acid (45) (250 mg, 0.44 mmol) was carried out in methyl alcohol (30 mL) using 10% palladium on carbon (0.5 g) with a pressure of 50 psi at room temperature for 2 hours. The product was filtered through a celite pad, and evaporated to give a crude product, which was purified by column chromatography on silica gel using a mixture of dichloromethane:methyl alcohol:30% ammonium hydroxide (10:5:1) to give 6-({5-[(4′-carbamimidoyl-biphenyl-4-ylamino)-methyl]-3-hydroxy-2-methyl-pyridin-4-ylmethyl}-amino)-hexanoic acid (46) (200 mg, 96% yield).

Workup

  1. customat room temperature
  2. customfor 2 hours
  3. filtrationThe product was filtered through a celite pad
  4. customevaporated
  5. customto give a crude product, which
  6. customwas purified by column chromatography on silica gel using
  7. additiona mixture of dichloromethane

Sources & evidence

ORD record
ord-432800be43d34d3abc1cf39a3bd00eb9
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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