Trifluoroacetic acid → HCID 68283476, compound

HRID 1527543Notes

Reaction equation

HRID 1527543 reaction equation
C(OC(=O)[NH:7][CH:8]([C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]([C:38](=[O:40])[CH3:39])[CH:30]=1)[C:9]([N:11]1[CH2:15][C@H:14]([F:16])[CH2:13][C@H:12]1[C:17](=[O:28])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[F:27])=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:26][C:22]1[C:21]([F:27])=[C:20]([CH:25]=[CH:24][CH:23]=1)[CH2:19][NH:18][C:17]([C@@H:12]1[CH2:13][C@@H:14]([F:16])[CH2:15][N:11]1[C:9](=[O:10])[CH:8]([C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]([C:38](=[O:40])[CH3:39])[CH:30]=1)[NH2:7])=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 68284521HCID 68284521, compound

Product 1

HCID 68283476HCID 68283476, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of {1-(1-acetyl-1H-indol-3-yl)-2-[(2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester (102 mg, 0.173 mmol) and TFA (66.7 μL, 0.866 mmol) in CH2Cl2 (0.58 mL) was stirred at 23° C. overnight. TFA (66.7 μL, 0.866 mmol) was again added and the reaction mixture was stirred at 23° C. for an additional 4 h to complete the reaction. Solvents were removed in vacuo and the crude residue was purified by preparative HPLC (Waters SunFire C180 DB, 5 μm, 19×50, eluent: 5% CH3CN/95% H2O to 100% CH3CN in 17 min, CH3CN and H2O containing 0.1% of TFA, flow 20 mL/min) to give after lyophilization of the purified fractions the desired material. MS (LC-MS): 487.1 [M−H]−; tR (HPLC conditions b): 3.19 min.

Workup

  1. customthe reaction
  2. customSolvents were removed in vacuo
  3. customthe crude residue was purified by preparative HPLC (Waters SunFire C180 DB, 5 μm, 19×50, eluent: 5% CH3CN/95% H2O to 100% CH3CN in 17 min, CH3CN and H2O containing 0.1% of TFA, flow 20 mL/min)
  4. customto give after lyophilization of the
  5. custompurified fractions the desired material
  6. custom3.19 min.

Sources & evidence

ORD record
ord-b16b5deb626748c19723225e0d37beef
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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