4-tert-Butylcyclohexylamine → N-[(1S,2S,4R)-1-Benzyl-4-(4-tert-butylcyclohexylcarbamoyl)-2-hydroxypentyl]-2-fluoro-3,5-bis-(2-oxopyrrolidin-1-yl)benzamide

HRID 1612503Notes

Reaction equation

HRID 1612503 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.[C:31]([CH:35]1[CH2:40][CH2:39][CH:38]([NH2:41])[CH2:37][CH2:36]1)([CH3:34])([CH3:33])[CH3:32].[F:42][C:43]1[C:66]([N:67]2[CH2:71][CH2:70][CH2:69][C:68]2=[O:72])=[CH:65][C:64]([N:73]2[CH2:77][CH2:76][CH2:75][C:74]2=[O:78])=[CH:63][C:44]=1[C:45]([NH:47][C@H:48]([C@@H:56]1[CH2:60][C@@H:59]([CH3:61])[C:58](=[O:62])[O:57]1)[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:46]>>[CH2:49]([C@H:48]([NH:47][C:45](=[O:46])[C:44]1[CH:63]=[C:64]([N:73]2[CH2:77][CH2:76][CH2:75][C:74]2=[O:78])[CH:65]=[C:66]([N:67]2[CH2:71][CH2:70][CH2:69][C:68]2=[O:72])[C:43]=1[F:42])[C@@H:56]([OH:57])[CH2:60][C@H:59]([C:58](=[O:62])[NH:41][CH:38]1[CH2:37][CH2:36][CH:35]([C:31]([CH3:34])([CH3:32])[CH3:33])[CH2:40][CH2:39]1)[CH3:61])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

4

Reactant 3

HCID 793964-tert-ButylcyclohexylamineHCID 69507916[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-carbamic acid t-butyl esterHCID 695896942-Fluoro-N-[(S)-1-((2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl)-2-phenylethyl]-3,5-bis-(2-oxopyrrolidin-1-yl)benzamide

Product 1

HCID 58583643N-[(1S,2S,4R)-1-Benzyl-4-(4-tert-butylcyclohexylcarbamoyl)-2-hydroxypentyl]-2-fluoro-3,5-bis-(2-oxopyrrolidin-1-yl)benzamide

Procedure

Prepared in an analogous manner to D1 from 4-tert-butylcyclohexylamine and 2-fluoro-N-[(S)-1-((2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl)-2-phenylethyl]-3,5-bis-(2-oxopyrrolidin-1-yl)benzamide (D50).

Sources & evidence

ORD record
ord-052e338d0b5047efba02b6113a145c53
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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