methyl (S)-2-amino-3-(4-butoxy-phenyl)-propionate → tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methylcarbamoyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoate

HRID 1779174Notes

Reaction equation

HRID 1779174 reaction equation
N[C@@H]([CH2:7][C:8]1[CH:13]=CC(OCCCC)=C[CH:9]=1)C(NC)=O.N[C@@H](CC1C=CC(OCCCC)=CC=1)C(OC)=O.[CH2:37]([O:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][C@H:49]([NH:54][C:55]([C@@H:57](/[CH:67]=[CH:68]/[CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][C:75]([F:84])([F:83])[CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH3:82])[C@@:58]([OH:66])([CH2:62][CH2:63][O:64][CH3:65])[C:59]([OH:61])=[O:60])=[O:56])[C:50](=[O:53])[NH:51][CH3:52])=[CH:44][CH:43]=1)[CH2:38][CH2:39][CH3:40]>>[CH2:37]([O:41][C:42]1[CH:43]=[CH:44][C:45]([CH2:48][C@H:49]([NH:54][C:55]([C@@H:57](/[CH:67]=[CH:68]/[CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][C:75]([F:83])([F:84])[CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH3:82])[C@@:58]([OH:66])([CH2:62][CH2:63][O:64][CH3:65])[C:59]([O:61][C:8]([CH3:13])([CH3:9])[CH3:7])=[O:60])=[O:56])[C:50](=[O:53])[NH:51][CH3:52])=[CH:46][CH:47]=1)[CH2:38][CH2:39][CH3:40]

Participants

4

Reactant 3

HCID 68030835methyl (S)-2-amino-3-(4-butoxy-phenyl)-propionateHCID 90060276(E)-(2S,3S)-3-[(S)-2-(4-Butoxy-phenyl)-1-methylcarbamoyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acidHCID 90060342(S)-2-amino-3-(4-butoxy-phenyl)-N-methyl-propionamide

Product 1

HCID 131734850tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methylcarbamoyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoate

Procedure

tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methylcarbamoyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoate (PSI (LC/MS positive mode) ink 739 (M+H); Rt 2.72 min.) was synthesized using (S)-2-amino-3-(4-butoxy-phenyl)-N-methyl-propionamide and the conditions at 50° C. for 2.5 days instead of methyl (S)-2-amino-3-(4-butoxy-phenyl)-propionate and the conditions in Step B-7′. (E)-(2S,3S)-3-[(S)-2-(4-Butoxy-phenyl)-1-methylcarbamoyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid (No. 5514404) was synthesized under conditions similar to those in the following Step B-8′.

Workup

  1. custom5514404) was synthesized under conditions similar to those in the following Step

Sources & evidence

ORD record
ord-068b255960c740769d10cda49f124120
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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