Trifluoroacetic acid → HCID 57520080, compound

HRID 1527531Notes

Reaction equation

HRID 1527531 reaction equation
C([O:5][C:6](=[O:38])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][NH:14][C:15]([C@@H:17]1[CH2:21][C@@H:20]([F:22])[CH2:19][N:18]1[C:23](=[O:37])[NH:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([C:34](=[O:36])[NH2:35])[CH:26]=1)=[O:16])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CCOCC>[C:34]([N:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:25]([NH:24][C:23]([N:18]2[CH2:19][C@H:20]([F:22])[CH2:21][C@H:17]2[C:15]([NH:14][CH2:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([OH:38])=[O:5])=[O:16])=[O:37])=[CH:26]1)(=[O:36])[NH2:35]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68284472HCID 68284472, compound

Product 1

HCID 57520080HCID 57520080, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-({[(2S,4R)-1-(1-carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-2-carbonyl]-amino}-methyl)-benzoic acid tert-butyl ester (prepared according to Scheme D1 using 2-aminomethyl-benzoic acid tert-butyl ester) (76 mg, 0.145 mm) in CH2Cl2 (1 mL) was added TFA (168 μl, 2.18 mmol) and the resulting solution was stirred at RT overnight. The crude mixture was concentrated to give a solid which was suspended in Et2O and filtered to give the desired material. MS (LC-MS): 468.1 [M+H]+, 490.1 [M+Na]+, 957.2 [2M+Na]+, 466.1 [M−H]−, 423.1 [M−CONH2]−, tR (HPLC conditions a): 2.64 min.

Workup

  1. concentrationThe crude mixture was concentrated
  2. customto give a solid which
  3. filtrationfiltered

Sources & evidence

ORD record
ord-9507967c72f54452a79eca0dcce58a61
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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