Hydrochloric Acid → HCID 68283753, compound

HRID 1527577Notes

Reaction equation

HRID 1527577 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[N:12]([CH2:14][C:15]([N:17]1[C@H:22]([C:23](=[O:34])[NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=3[F:33])[CH2:21][C@@H:20]3[C@H:18]1[CH2:19]3)=[O:16])[CH:11]=[C:10]2[C:35](=[O:37])[CH3:36])=[O:4].[Li+].[OH-].Cl>C1COCC1.O>[C:35]([C:10]1[C:9]2[C:13](=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[CH:7][CH:8]=2)[N:12]([CH2:14][C:15]([N:17]2[C@H:22]([C:23](=[O:34])[NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=3[F:33])[CH2:21][C@@H:20]3[C@H:18]2[CH2:19]3)=[O:16])[CH:11]=1)(=[O:37])[CH3:36]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68283809HCID 68283809, compound

Product 1

HCID 68283753HCID 68283753, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-acetyl-1-{2-[(1R,3S,5R)-3-(3-chloro-2-fluoro-benzylcarbamoyl)-2-aza-bicyclo[3.1.0]hex-2-yl]-2-oxo-ethyl}-1H-indole-7-carboxylic acid methyl ester Example 541 (110 mg, 0.209 mmol) in THF (3 mL) and water (0.3 mL) was added 2N LiOH (1.05 mL, 2.09 mmol). Stirring of the reaction mixture was continued at RT for 18 h. A 1N HCl solution was added to adjust to pH=2-3 and the resulting aqueous suspension was filtered. The solid was washed with water then dried in vacuo. The residue was purified by preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, flow: 40 mL/min, eluent: 20-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA) to afford after lyophilization of the purified fractions the title compound as a white solid. MS (LC/MS): 512 [M+H]+; tR (HPLC conditions k): 3.34 min.

Workup

  1. filtrationthe resulting aqueous suspension was filtered
  2. washThe solid was washed with water
  3. customthen dried in vacuo
  4. customThe residue was purified by preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm, flow: 40 mL/min, eluent: 20-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-b2461f90cd2e40aeabb7453b9aba3fcf
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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