Dichloromethane → HCID 178472561, compound

HRID 238905Notes

Reaction equation

HRID 238905 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[C@@H:5]([NH:7][C@H:8]([C:23](=[O:40])[N:24]([C:26]1[N:30](CC2C=CC(OC)=CC=2)[N:29]=[N:28][N:27]=1)[CH3:25])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[CH:12][CH:11]=1)[CH3:6])[CH3:2].C(Cl)Cl>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4](=[O:41])[C@@H:5]([NH:7][C@H:8]([C:23](=[O:40])[N:24]([CH3:25])[C:26]1[NH:30][N:29]=[N:28][N:27]=1)[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[CH:14][CH:15]=1)[CH3:6])[CH3:2]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 58280554(S)-2-((S)-2-(3'-chloro-biphenyl-4-yl)-1-{[1-(4-methoxy-benzyl)-1H-tetrazol-5-yl]-methyl-carbamoyl}ethylamino)-propionic acid ethyl ester

Product 1

HCID 178472561HCID 178472561, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Next, (S)-2-((S)-2-(3′-chloro-biphenyl-4-yl)-1-{[1-(4-methoxy-benzyl)-1H-tetrazol-5-yl]-methyl-carbamoyl}-ethylamino)-propionic acid ethyl ester (260 mg, 0.451 mmol) was dissolved in TFA (5 mL) and DCM (5 mL) and stirred at 50° C. for 12 hours and at 75° C. for 5 hours. The reaction mixture was concentrated under reduced pressure to give (S)-2-{(S)-2-(3′-chloro-biphenyl-4-yl)-1-[methyl-(1H-tetrazol-5-yl)-carbamoyl]-ethylamino}-propionic acid ethyl ester (120 mg). MS: m/z (MH+) 457; HPLC retention time 0.95 min (HPLC condition C).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3b3830017f1c4d9992141db198e595d7
Source dataset
uspto-grants-2014_02
Patent number
US08642635B2

Reaction notes

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