4,4-Dimethylcyclohexan-1-amine → N-[(1S,2S,4R)-1-Benzyl-4-(4,4-dimethylcyclohexylcarbamoyl)-2-hydroxypentyl]-3-isopropoxy-5-(2-oxopyrrolidin-1-yl)benzamide

HRID 1612500Notes

Reaction equation

HRID 1612500 reaction equation
C(OC(=O)N[C@@H](CC1C=CC=CC=1)[C@@H](O)C[C@H](C(=O)NCCC(C)(C)C)C)(C)(C)C.[CH3:31][C:32]1([CH3:39])[CH2:37][CH2:36][CH:35]([NH2:38])[CH2:34][CH2:33]1.[CH:40]([O:43][C:44]1[CH:45]=[C:46]([CH:65]=[C:66]([N:68]2[CH2:72][CH2:71][CH2:70][C:69]2=[O:73])[CH:67]=1)[C:47]([NH:49][C@H:50]([C@@H:58]1[CH2:62][C@@H:61]([CH3:63])[C:60](=[O:64])[O:59]1)[CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:48])([CH3:42])[CH3:41]>>[CH2:51]([C@H:50]([NH:49][C:47](=[O:48])[C:46]1[CH:65]=[C:66]([N:68]2[CH2:72][CH2:71][CH2:70][C:69]2=[O:73])[CH:67]=[C:44]([O:43][CH:40]([CH3:42])[CH3:41])[CH:45]=1)[C@@H:58]([OH:59])[CH2:62][C@H:61]([C:60](=[O:64])[NH:38][CH:35]1[CH2:36][CH2:37][C:32]([CH3:39])([CH3:31])[CH2:33][CH2:34]1)[CH3:63])[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Participants

4

Reactant 3

HCID 4210544,4-Dimethylcyclohexan-1-amineHCID 69507916[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-carbamic acid t-butyl esterHCID 695897653-Isopropoxy-N-[(S)-1-((2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl)-2-phenylethyl]-5-(2-oxopyrrolidin-1-yl)benzamide

Product 1

HCID 10312223N-[(1S,2S,4R)-1-Benzyl-4-(4,4-dimethylcyclohexylcarbamoyl)-2-hydroxypentyl]-3-isopropoxy-5-(2-oxopyrrolidin-1-yl)benzamide

Procedure

Prepared in an analogous manner to D1 from 4,4-dimethylcyclohexylamine (D53) and 3-isopropoxy-N-[(S)-1-((2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl)-2-phenylethyl]-5-(2-oxopyrrolidin-1-yl)benzamide (D49).

Sources & evidence

ORD record
ord-1656c004f8794ba6bf499aaab6a7e2ef
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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