Trifluoroacetic acid → HCID 89719307, compound

HRID 63727Notes

Reaction equation

HRID 63727 reaction equation
[CH3:1][O:2][C:3](=[O:46])[C@@H:4]([NH:23][C:24](=[O:45])[C:25]1[C:30]([Cl:31])=[CH:29][C:28]([O:32][CH2:33][CH2:34][CH2:35][NH:36]C(OC(C)(C)C)=O)=[CH:27][C:26]=1[Cl:44])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:22])[C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:21])=[CH:8][CH:7]=1.C(O)(C(F)(F)F)=O>ClCCl>[CH3:1][O:2][C:3](=[O:46])[C@@H:4]([NH:23][C:24](=[O:45])[C:25]1[C:26]([Cl:44])=[CH:27][C:28]([O:32][CH2:33][CH2:34][CH2:35][NH2:36])=[CH:29][C:30]=1[Cl:31])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:22])[C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:21])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89717547(S)-2-[4-(3-tert-butoxycarbonylaminopropoxy)-2,6-dichlorobenzoylamino]-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester

Product 1

HCID 89719307HCID 89719307, compoundYield 118.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-[4-(3-tert-butoxycarbonylaminopropoxy)-2,6-dichlorobenzoylamino]-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester (7.5 g, 7.98 mmol) in dichloromethane (100 mL) was added an excess of TFA (9.12 g, 5.9 mL, 80 mmol) at room temperature. The resulting solution was stirred for 15 h. Then, the solvent was removed under vacuum and the residue was azeotrophed one time with toluene. After drying under high vacuum, 5.8 g (99%) of (S)-2-[4-(3-aminopropoxy)-2,6-dichlorobenzoylamino]-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester was obtained as a white solid. ES(+)-HRMS m/e calcd. for C27H25Cl4N3O5 (M+H)+ 612.0621, obsd. 612.0619.

Workup

  1. customThen, the solvent was removed under vacuum
  2. customAfter drying under high vacuum

Sources & evidence

ORD record
ord-c51cf0cc9a4948cf95c67713976f5da1
Source dataset
uspto-grants-2016_09
Patent number
US09447035B2

Reaction notes

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