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

HRID 1612502Notes

Reaction equation

HRID 1612502 reaction equation
C(O[C:6](=[O:30])[NH:7][C@@H:8]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])[NH:14][CH2:15][CH2:16][C:17]([CH3:20])(C)C)[CH3:12])(C)(C)C.C1(N)CCC1.[F:36][C:37]1[C:60]([N:61]2[CH2:65][CH2:64][CH2:63][C:62]2=[O:66])=[CH:59][C:58]([N:67]2[CH2:71][CH2:70][CH2:69][C:68]2=[O:72])=[CH:57][C:38]=1C(N[C@H]([C@@H]1C[C@@H](C)C(=O)O1)CC1C=CC=CC=1)=O>>[CH2:23]([C@H:8]([NH:7][C:6](=[O:30])[C:38]1[CH:57]=[C:58]([N:67]2[CH2:71][CH2:70][CH2:69][C:68]2=[O:72])[CH:59]=[C:60]([N:61]2[CH2:65][CH2:64][CH2:63][C:62]2=[O:66])[C:37]=1[F:36])[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])[NH:14][CH:15]1[CH2:16][CH2:17][CH2:20]1)[CH3:12])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 75645CyclobutylamineHCID 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 10218586N-[(1S,2S,4R)-1-Benzyl-4-(cyclobutylcarbamoyl)-2-hydroxypentyl]-2-fluoro-3,5-bis-(2-oxopyrrolidin-1-yl)benzamide

Procedure

Prepared in an analogous manner to D1 from cyclobutylamine 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-0280fb60fb364e4682a3fb0c9e58ce09
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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