1-(S)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-2-(S)-phenyl-3-(R)-(((S)-(2-pyrrolidon-5-yl))-methylamino)cyclopentane → 1-(R)-(1-(S)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-2-(R)-phenyl-3-(S)-(aminocarbonylmethylamino)cyclopentane

HRID 1289943Notes

Reaction equation

HRID 1289943 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:20][CH2:19][C@@H:18]([NH:21][CH2:22][C:23]([NH2:25])=[O:24])[C@@H:17]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.COC1C=CC(CN[C@@H]2CC[C@@H](C(OC)=O)[C@@H]2C2C=CC(F)=CC=2)=CC=1.COC1C=CC(CN[C@H]2CC[C@@H](C(OC)=O)[C@@H]2C2C=CC(F)=CC=2)=CC=1.COC1C=CC(CN[C@H]2CC[C@H](C(OC)=O)[C@H]2C2C=CC(F)=CC=2)=CC=1.COC1C=CC(CN[C@@H]2CC[C@H](C(OC)=O)[C@H]2C2C=CC(F)=CC=2)=CC=1.COC1C=CC(N2C=NN=N2)=CC=1CN[C@H]1CC[C@@H](C(OC)=O)[C@@H]1C1C=CC(F)=CC=1.COC1C=CC(N2C=NN=N2)=CC=1CN[C@H]1CC[C@H](C(OC)=O)[C@H]1C1C=CC(F)=CC=1.FC(F)(F)C1C=C(C(N[C@H]2CC[C@@H](C(OC)=O)[C@@H]2C2C=CC(F)=CC=2)=O)C=C(C(F)(F)F)C=1.FC(F)(F)C1C=C(C(N([C@H]2CC[C@@H](C(OC)=O)[C@@H]2C2C=CC(F)=CC=2)C)=O)C=C(C(F)(F)F)C=1.FC(F)(F)C1C=C(C(N[C@H]2CC[C@@H](C(OC)=O)[C@@H]2C2C=CC(F)=CC=2)C)C=C(C(F)(F)F)C=1.FC(F)(F)C1C=C([C@H](O[C@H]2CC[C@@H](N([C@@H]3NC(=O)CC3)C)[C@@H]2C2C=CC=CC=2)C)C=C(C(F)(F)F)C=1>>[F:1][C:2]([F:32])([F:33])[C:3]1[CH:4]=[C:5]([C@@H:13]([O:15][C@@H:16]2[CH2:20][CH2:19][C@H:18]([NH:21][CH2:22][C:23]([NH2:25])=[O:24])[C@H:17]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1

Participants

12

Reactant 11

HCID 228856361-(S)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-2-(S)-phenyl-3-(R)-(((S)-(2-pyrrolidon-5-yl))-methylamino)cyclopentaneHCID 22885643methyl 3-(S)-(1-(RS)-(3,5-bis(trifluoromethyl)phenyl)ethylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylateHCID 22885645methyl 3-(S)-((3,5-bis(trifluoromethyl)phenyl)carbonylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylateHCID 22885648methyl 3-(S)-(N-((3,5-bis(trifluoromethyl)phenyl)carbonyl)-N-methylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylateHCID 22885804methyl 3-(S)-((4-methoxyphenyl)methylamino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylateHCID 542824601-(S)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-2-(S)-phenyl-3-(R)-(aminocarbonylmethylamino)cyclopentaneHCID 67592890methyl 3-(S)-((2-methoxy-5-(1-tetrazolyl)phenyl)methylamino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylateHCID 67666832methyl 3-(R)-((4-methoxyphenyl)methylamino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylateHCID 67666845methyl 3-(R)-((4-methoxyphenyl)methylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylateHCID 67666929methyl 3-(S)-((4-methoxyphenyl)methylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylateHCID 67669017methyl 3-(S)-((2-methoxy-5-(1-tetrazolyl)phenyl)methylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylate

Product 1

HCID 228856331-(R)-(1-(S)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-2-(R)-phenyl-3-(S)-(aminocarbonylmethylamino)cyclopentane

Procedure

##STR10## 1-(S)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-2-(S)-phenyl-3-(R)-(aminocarbonylmethylamino)cyclopentane; ##STR11## methyl 3-(R)-((4-methoxyphenyl)methylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylate; ##STR12## methyl 3-(S)-((4-methoxyphenyl)methylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylate; ##STR13## methyl 3-(S)-((4-methoxyphenyl)methylamino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylate; ##STR14## methyl 3-(R)-((4-methoxyphenyl)methylamino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylate; ##STR15## methyl 3-(S)-((2-methoxy-5-(1-tetrazolyl)phenyl)methylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylate; ##STR16## methyl 3-(S)-((2-methoxy-5-(1-tetrazolyl)phenyl)methylamino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylate; ##STR17## methyl 3-(S)-((3,5-bis(trifluoromethyl)phenyl)carbonylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylate; ##STR18## methyl 3-(S)-(N-((3,5-bis(trifluoromethyl)phenyl)carbonyl)-N-methylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylate; ##STR19## methyl 3-(S)-(1-(RS)-(3,5-bis(trifluoromethyl)phenyl)ethylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylate; ##STR20## 1-(S)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-2-(S)-phenyl-3-(R)-(((S)-(2-pyrrolidon-5-yl))-methylamino)cyclopentane; ##STR21## 1-(S)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-2-(S)-phenyl-3-(R)-(3-(5-oxo-1H,4H-1,2,4-triazolo)methylamino)cyclopentane;

Sources & evidence

ORD record
ord-c84f7e4669174bcaa256a67976b4fddc
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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