Tert-butyl (2S)-2-amino-4-(methylsulfanyl)butanoate → Cyclopentyl (2S)-2-{3-(4-fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyrid-2-oylamino}-4-methylsulfanylbutyrate

HRID 1251924Notes

Reaction equation

HRID 1251924 reaction equation
F[C:2]1C=CC(CCC2C(C(O)=O)=NC(OC(C3C=CC(F)=CC=3)CC3N(C)C=NC=3)=CC=2)=C[CH:3]=1.[F:35][C:36]1[CH:80]=[CH:79][C:39]([CH2:40][CH2:41][C:42]2[C:43]([C:64]([NH:66][C@@H:67]([CH2:75][CH2:76][S:77][CH3:78])[C:68]([O:70][C:71](C)([CH3:73])[CH3:72])=[O:69])=[O:65])=[N:44][C:45]([O:48][CH:49]([C:57]3[CH:62]=[CH:61][C:60]([F:63])=[CH:59][CH:58]=3)[CH2:50][C:51]3[N:55]([CH3:56])[CH:54]=[N:53][CH:52]=3)=[CH:46][CH:47]=2)=[CH:38][CH:37]=1.C1(OC(=O)[C@H](CCSC)N)CCCC1.C(OC(=O)[C@H](CCSC)N)(C)(C)C>>[F:35][C:36]1[CH:37]=[CH:38][C:39]([CH2:40][CH2:41][C:42]2[C:43]([C:64]([NH:66][C@@H:67]([CH2:75][CH2:76][S:77][CH3:78])[C:68]([O:70][CH:71]3[CH2:72][CH2:3][CH2:2][CH2:73]3)=[O:69])=[O:65])=[N:44][C:45]([O:48][CH:49]([C:57]3[CH:62]=[CH:61][C:60]([F:63])=[CH:59][CH:58]=3)[CH2:50][C:51]3[N:55]([CH3:56])[CH:54]=[N:53][CH:52]=3)=[CH:46][CH:47]=2)=[CH:79][CH:80]=1

Participants

5

Reactant 4

HCID 7010638Tert-butyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 9939436tert-butyl (2S)-2-{3-(4-fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyrid-2-oylamino}-4-methylsulfanylbutyrateHCID 183243783-(4-Fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyridin-2-carboxylic acidHCID 53747326cyclopentyl (2S)-2-amino-4-(methylsulfanyl)butanoate

Product 1

HCID 9831119Cyclopentyl (2S)-2-{3-(4-fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyrid-2-oylamino}-4-methylsulfanylbutyrate

Procedure

The title compound was prepared from 3-(4-fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyridin-2-carboxylic acid by a similar route to that described for the preparation of tert-butyl (2S)-2-{3-(4-fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyrid-2-oylamino}-4-methylsulfanylbutyrate but using L-methionine cyclopentyl ester rather than L-methionine-tert-butyl ester.

Sources & evidence

ORD record
ord-1365eb6856d2475381fb2e2819791fea
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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