methyl 4-[(1S)-1-({[5-bromo-4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate → 4-[(1S)-1-({[5-bromo-4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoic acid

HRID 870044Notes

Reaction equation

HRID 870044 reaction equation
[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([NH:9][C@H:10]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=2)[CH3:11])=[O:8])[C:3]=1[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=1>CCOC(C)=O.CCCCCC>[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([NH:9][C@H:10]([C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=2)[CH3:11])=[O:8])[C:3]=1[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=1

Participants

3

Reactant 1

HCID 57900972methyl 4-[(1S)-1-({[5-bromo-4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

Product 1

HCID 249525784-[(1S)-1-({[5-bromo-4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Methyl 4-[(S)-1-({[5-bromo-4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate from Example 4, Step 1 (25.0 mg, 0.0507 mmol) was reacted under conditions similar to Example 1, Step 11. After trituration of the crude product in 1:1 EtOAc/hexane, the desired product was obtained as an off-white solid. MS (−APCI): m/z 476 (M−1)−.

Sources & evidence

ORD record
ord-5bb0397b380245f28e9335c5252bb57a
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

Loading…