3,4-Di-(4-fluorobenzyloxy)benzoic acid → (2S)-2-[[3,4-bis[(4-fluorophenyl)methoxy]benzoyl]amino]-N-(3-hydroxy-4-methoxy-phenyl)-N'-trityl-pentanediamide

HRID 1860345Notes

Reaction equation

HRID 1860345 reaction equation
C1C2C(C[O:15][C:16]([NH:18][C@H:19]([C:44]([NH:46][C:47]3[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[C:49]([OH:55])[CH:48]=3)=[O:45])[CH2:20][CH2:21][C:22](=[O:43])[NH:23][C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=O)C3C(=CC=CC=3)C=2C=CC=1.[F:56][C:57]1[CH:82]=[CH:81][C:60]([CH2:61][O:62][C:63]2[CH:64]=[C:65]([CH:69]=[CH:70][C:71]=2[O:72][CH2:73][C:74]2[CH:79]=[CH:78][C:77]([F:80])=[CH:76][CH:75]=2)C(O)=O)=[CH:59][CH:58]=1>>[F:56][C:57]1[CH:82]=[CH:81][C:60]([CH2:61][O:62][C:63]2[CH:64]=[C:65]([CH:69]=[CH:70][C:71]=2[O:72][CH2:73][C:74]2[CH:79]=[CH:78][C:77]([F:80])=[CH:76][CH:75]=2)[C:16]([NH:18][C@H:19]([C:44]([NH:46][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[C:49]([OH:55])[CH:48]=2)=[O:45])[CH2:20][CH2:21][C:22](=[O:43])[NH:23][C:24]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:15])=[CH:59][CH:58]=1

Participants

3

Reactant 2

HCID 186270553,4-Di-(4-fluorobenzyloxy)benzoic acidHCID 22976129N-[Nalpha-(9-fluorenylmethoxycarbonyl)-Ndelta-trityl-L-glutaminyl]-3-hydroxy-4-methoxyaniline

Product 1

HCID 504874(2S)-2-[[3,4-bis[(4-fluorophenyl)methoxy]benzoyl]amino]-N-(3-hydroxy-4-methoxy-phenyl)-N'-trityl-pentanediamide

Procedure

The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-Nδ-trityl-L-glutaminyl]-3-hydroxy-4-methoxyaniline (642 mg, 0.9 mmol, example 109, step A) as described for example 109 (step B) using 3,4-di-(4-fluorobenzyloxy)benzoic acid (485 mg, 1.3 mmol) instead of N-(4-fluorobenzyl)indole-2-carboxylic acid. The crude material was purified by flash chromatography using successively 5%, 10% and 30% EtOAc/CH2Cl2 as the eluent. The title compound was obtained as white crystals (260 mg, 34%).

Workup

  1. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-aa23c12a7218480cb43f0872aa582902
Source dataset
uspto-grants-2003_03
Patent number
US06528655B1

Reaction notes

Loading…