(S)-2-(Biphenyl-3-ylamino)-3-(3,4,5-trimethoxy-phenyl)-propionic acid → (S)-2-(Biphenyl-3-ylamino)-3-(2,3,4-trimethoxyphenyl)-propionic acid

HRID 1920631Notes

Reaction equation

HRID 1920631 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]C2C=C(OC)C(OC)=C(OC)C=2)[C:9]([OH:11])=[O:10])[CH:2]=1.N[C@@H](C[C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([O:45][CH3:46])[C:38]=1[O:47][CH3:48])C(O)=O>>[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:41]2[CH:42]=[CH:37][C:38]([O:47][CH3:48])=[C:39]([O:45][CH3:46])[C:40]=2[O:43][CH3:44])[C:9]([OH:11])=[O:10])[CH:2]=1

Participants

3

Reactant 2

HCID 11384247(S)-2-(Biphenyl-3-ylamino)-3-(3,4,5-trimethoxy-phenyl)-propionic acidHCID 28182480(S)-2-Amino-3-(2,3,4-trimethoxy-phenyl)-propionic acid

Product 1

HCID 67492532(S)-2-(Biphenyl-3-ylamino)-3-(2,3,4-trimethoxyphenyl)-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 (S)-2-Amino-3-(2,3,4-trimethoxy-phenyl)-propionic acid. Purification by MPLC (CH3CN/H2O/TFA) afforded the title compound; ES-MS: 408.2 [M+H]+; HPLC: single peak at tR=9.42 min (System 1).

Workup

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

Sources & evidence

ORD record
ord-5bff472e669044f7bbade4efda60027f
Source dataset
uspto-grants-2012_05
Patent number
US08173128B2

Reaction notes

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