HCID 58636874, compound → Ammonium Hydroxide

HRID 1158951Notes

Reaction equation

HRID 1158951 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[C:13]([CH2:20][NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[C:14]([OH:19])[C:15]([CH3:18])=[N:16][CH:17]=2)=[CH:6][CH:5]=1)(=[NH:3])[NH2:2]>Cl>[OH-:19].[NH4+:2].[CH2:1]([O:19][C:14]1[C:15]([CH3:18])=[N:16][CH:17]=[C:12]([CH2:11][NH:10][C:7]2[CH:6]=[CH:5][C:4]([C:1](=[NH:2])[NH2:3])=[CH:9][CH:8]=2)[C:13]=1[CH2:20][NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 58636874HCID 58636874, compound

Product 2

HCID 14923Ammonium HydroxideYield 30%HCID 68644166HCID 68644166, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The hydrolysis of 6-({5-[(4-carbamimidoyl-phenylamino)-methyl]-3-hydroxy-2-methyl-pyridin-4 ylmethyl}-amino)-hexanoic acid (49) (100 mg, 0.2 mmol) was carried out in 6N hydrochloric acid for 2 hours. The solvent was then evaporated and the crude product purified by column chromatography on silica gel using a mixture of dichloromethane:methyl alcohol:30% ammonium hydroxide (5:3:1) as eluant to give 6-({3-benzyloxy-5-[(4-carbamimidoyl-phenylamino)-methyl]-2-methyl-pyridin-4-ylmethyl}-amino)-hexanoic acid (50).

Workup

  1. customThe solvent was then evaporated
  2. customthe crude product purified by column chromatography on silica gel using
  3. additiona mixture of dichloromethane

Sources & evidence

ORD record
ord-aeb648e583f347e49bae8e387f117695
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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