Trifluoroacetic acid → HCID 58742481, compound

HRID 722264Notes

Reaction equation

HRID 722264 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][C@@H:14]1[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C@H:15]1[NH:23][CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[O:12])=[CH:5]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:25]([CH2:24][NH:23][C@@H:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][C@H:14]1[NH:13][C:11]([C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)=[O:12])([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58742476HCID 58742476, compound

Product 1

HCID 58742481HCID 58742481, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl N-((1R,2R)-2-{[(5-chloro-1H-indol-2-yl)carbonyl]amino}-2,3-dihydro-1H-inden-1-yl)glycinate (Method 8, 230 mg, 0.52 mmol) was dissolved in DCM (10 mL). TFA (1 mL) was added and the reaction stirred at ambient temperature for 3 hours. Evaporation under reduced pressure, co-evaporation with CHCl3 (2×10 mL) and crystallization from EtOAc gave the title compound (85 mg, 36%) as a powder.

Workup

  1. customEvaporation under reduced pressure, co-evaporation
  2. customwith CHCl3 (2×10 mL) and crystallization from EtOAc

Sources & evidence

ORD record
ord-95542a2176694b2cb2266344b0140c1d
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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