Acetonitrile → (R)-2-(5-hydroxy-indol-1-yl)-propionic acid methyl ester

HRID 734394Notes

Reaction equation

HRID 734394 reaction equation
C[N:2]1[CH2:12][CH:11](C2C=CC=C(N=C=S)C=2)[C:10]2[CH:9]=[C:8]([OH:22])[C:7](Cl)=[CH:6][C:5]=2[CH2:4][CH2:3]1.[C:24]([OH:30])(C(F)(F)F)=[O:25].[C:31](#N)C>O>[CH3:31][O:30][C:24](=[O:25])[C@H:3]([N:2]1[C:5]2[C:10](=[CH:9][C:8]([OH:22])=[CH:7][CH:6]=2)[CH:11]=[CH:12]1)[CH3:4]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acid2×HCID 98195358-Chloro-5-(3-isothiocyanato-phenyl)-3-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol

Product 1

HCID 57845515(R)-2-(5-hydroxy-indol-1-yl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reverse Phase HPLC conditions: Column: YMC-Pack ProC18 (AS-300), 50×4.6 mm (I.D.), S-5 μm, 12 nm (No. 040506614); Mobile Phase: A: 0.1% TFA in Water; B: 0.1% TFA in Acetonitrile; Gradient: 90-5% A (10-95% B) in 7 min; Flow rate: 4.0 mL/min; Detector (UV): 220 nm. Retention time of the title compound: 2.54 min.

Sources & evidence

ORD record
ord-002b01f1cf5d4f8faf3d0b10b25340a9
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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