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

HRID 1612498Notes

Reaction equation

HRID 1612498 reaction equation
C(OC(=O)N[C@@H](CC1C=CC=CC=1)[C@@H](O)[CH2:10][C@H:11]([C:13](=O)[NH:14]CCC(C)(C)C)[CH3:12])(C)(C)C.C(N)C(C)C.[CH:36]([O:39][C:40]1[CH:41]=[C:42]([CH:61]=[C:62]([N:64]2[CH2:68][CH2:67][CH2:66][C:65]2=[O:69])[CH:63]=1)[C:43]([NH:45][C@H:46]([C@@H:54]1[CH2:58][C@@H:57]([CH3:59])[C:56](=[O:60])[O:55]1)[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:44])([CH3:38])[CH3:37]>>[CH2:47]([C@H:46]([NH:45][C:43](=[O:44])[C:42]1[CH:61]=[C:62]([N:64]2[CH2:68][CH2:67][CH2:66][C:65]2=[O:69])[CH:63]=[C:40]([O:39][CH:36]([CH3:37])[CH3:38])[CH:41]=1)[C@@H:54]([OH:55])[CH2:58][C@H:57]([C:56](=[O:60])[NH:14][CH2:13][CH:11]([CH3:12])[CH3:10])[CH3:59])[C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

Participants

4

Reactant 3

HCID 6558IsobutylamineHCID 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 10218221N-[(1S,2S,4R)-1-Benzyl-4-(isobutylcarbamoyl)-2-hydroxypentyl]-3-isopropoxy-5-(2-oxopyrrolidin-1-yl)benzamide

Procedure

Prepared in an analogous manner to D1 from isobutylamine 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-c2e496e209794a48919473c60e5e1acf
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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