Hydrochloric Acid → (2S)-2-[(3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethyl-amino]propyl}-1H-indole-7-carbonyl)amino]-4-methylpentanoic acid

HRID 1351939Notes

Reaction equation

HRID 1351939 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:35])[CH2:9][NH:10][C@H:11]([CH3:34])[CH2:12][C:13]2[C:21]3[C:16](=[C:17]([C:22]([NH:24][C@@H:25]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:26]([O:28]C)=[O:27])=[O:23])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C([O-])=O.[OH-].[K+].Cl>O.CO>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:35])[CH2:9][NH:10][C@H:11]([CH3:34])[CH2:12][C:13]2[C:21]3[C:16](=[C:17]([C:22]([NH:24][C@@H:25]([CH2:30][CH:31]([CH3:32])[CH3:33])[C:26]([OH:28])=[O:27])=[O:23])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 84468TrifluoroacetateHCID 86604019methyl (2S)-2-[(3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indole-7-carbonyl)amino]-4-methyl-pentanoate

Product 1

HCID 69712139(2S)-2-[(3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethyl-amino]propyl}-1H-indole-7-carbonyl)amino]-4-methylpentanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl (2S)-2-[(3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indole-7-carbonyl)amino]-4-methyl-pentanoate.trifluoroacetate (20 mg, 0.0326 mmol) and potassium hydroxide (60 mg, 1.1 mmol) in water (0.5 mL) and methanol (2 mL) is stirred at room temperature for 3 hours. The mixture is acidified with 1N hydrochloric acid, and purified by preparative reversed phase HPLC (octadecylsilyl, trifluoroacetic acid/acetonitrile/water) to give the desired (2S)-2-[(3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethyl-amino]propyl}-1H-indole-7-carbonyl)amino]-4-methylpentanoic acid.trifluoroacetate (18 mg, yield: 92%).

Workup

  1. custompurified by preparative reversed phase HPLC (octadecylsilyl, trifluoroacetic acid/acetonitrile/water)

Sources & evidence

ORD record
ord-7b18265c391b4e3ab1ddc2de2b715378
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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