O-benzyl-L-tyrosine → (S)-3-(4-Benzyloxy-phenyl)-2-(biphenyl-3-ylamino)-propionic acid

HRID 1765941Notes

Reaction equation

HRID 1765941 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](N[C@@H](CC2C=C(OC)C(OC)=C(OC)C=2)C(O)=O)[CH:2]=1.[NH2:31][C@@H:32]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:39][CH:38]=1)[C:33]([OH:35])=[O:34]>>[CH2:44]([O:43][C:40]1[CH:41]=[CH:42][C:37]([CH2:36][C@H:32]([NH:31][C:27]2[CH:26]=[C:25]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:30]=[CH:29][CH:28]=2)[C:33]([OH:35])=[O:34])=[CH:38][CH:39]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

3

Reactant 2

HCID 725701O-benzyl-L-tyrosineHCID 11384247(S)-2-(Biphenyl-3-ylamino)-3-(3,4,5-trimethoxy-phenyl)-propionic acid

Product 1

HCID 67492656(S)-3-(4-Benzyloxy-phenyl)-2-(biphenyl-3-ylamino)-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-(4-benzyloxy-phenyl)-propionic acid (O-benzyl-L-tyrosine). Purification by MPLC (CH3CN/H2O/TFA) afforded the title compound; ES-MS: 424.3 [M+H]+; HPLC: single peak at tR=10.40 min (System 1).

Workup

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

Sources & evidence

ORD record
ord-292bff33f2b6460ab730e07de105895d
Source dataset
uspto-grants-2007_06
Patent number
US07229617B2

Reaction notes

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