Hydrochloric Acid → 4-[(1S)-1-({[2,5-dichloro-4-(3-chlorobenzoyl)-3-thienyl]carbonyl}amino)ethyl]benzoic acid

HRID 870055Notes

Reaction equation

HRID 870055 reaction equation
[Cl:1][C:2]1[S:3][C:4]([Cl:31])=[C:5]([C:22](=[O:30])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[C:6]=1[C:7]([NH:9][C@H:10]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1)[CH3:11])=[O:8].Cl>>[Cl:1][C:2]1[S:3][C:4]([Cl:31])=[C:5]([C:22](=[O:30])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[C:6]=1[C:7]([NH:9][C@H:10]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=1)[CH3:11])=[O:8]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 57900990methyl 4-[(1S)-1-({[2,5-dichloro-4-(3-chlorobenzoyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

Product 1

HCID 249529264-[(1S)-1-({[2,5-dichloro-4-(3-chlorobenzoyl)-3-thienyl]carbonyl}amino)ethyl]benzoic acid

Procedure

Methyl 4-[(1S)-1-({[2,5-dichloro-4-(3-chlorobenzoyl)-3-thienyl]carbonyl}amino)ethyl]benzoate from Example 10, Step 1 (73.0 mg, 0.147 mmol) was reacted under conditions similar to Example 1, Step 11. The reaction mixture was neutralized with 25% aq. NH4OAc (instead of an acidification with 1N HCl). The crude was purified by chromatography on silica gel (35:65 EtOAc/hexane containing 0.25% AcOH) to afford the desired product as an off-white solid. MS (−APCI): m/z 480 (M−1)−.

Workup

  1. customThe crude was purified by chromatography on silica gel (35:65 EtOAc/hexane containing 0.25% AcOH)

Sources & evidence

ORD record
ord-426536f23bf64413b594141532f2d506
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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