O-Methyl-L-Tyrosine → (S)-2-(Biphenyl-3-ylamino)-3-(4-methoxy-phenyl)-propionic acid

HRID 1920628Notes

Reaction equation

HRID 1920628 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C@@H:8]([CH2:12][C:13]2[CH:18]=[C:17](OC)[C:16]([O:21][CH3:22])=[C:15](OC)[CH:14]=2)[C:9]([OH:11])=[O:10])[CH:2]=1.COC1C=CC(C[C@@H](C(O)=O)N)=CC=1>>[C:1]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C@@H:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:21][CH3:22])=[CH:15][CH:14]=2)[C:9]([OH:11])=[O:10])[CH:2]=1

Participants

3

Reactant 2

HCID 2723935O-Methyl-L-TyrosineHCID 11384247(S)-2-(Biphenyl-3-ylamino)-3-(3,4,5-trimethoxy-phenyl)-propionic acid

Product 1

HCID 67492714(S)-2-(Biphenyl-3-ylamino)-3-(4-methoxy-phenyl)-propionic acid

Procedure

The title compound is prepared as described for (S)-2-(Biphenyl-3-ylamino)-3-(3,4,5-trimethoxy-phenyl)-propionic acid (example 1) but using O-methyl-L-tyrosine (Bachem). Purification by MPLC (CH3CN/H2O/TFA) afforded the title compound; ES-MS: 348.3 [M+H]+; HPLC: single peak at tR=9.52 min (System 1).

Workup

  1. customThe title compound is prepared
  2. customPurification by MPLC (CH3CN/H2O/TFA)

Sources & evidence

ORD record
ord-90d0e67d02df4817b106391e8aed6703
Source dataset
uspto-grants-2012_05
Patent number
US08173128B2

Reaction notes

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