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

HRID 1612499Notes

Reaction equation

HRID 1612499 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(CN)CC1.[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(N[C@H]([C@@H]1C[C@@H](C)C(=O)O1)CC1C=CC=CC=1)=O)([CH3:38])[CH3:37]>>[CH2:23]([C@H:8]([NH:7][C:6](=[O:30])[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]([CH3:38])[CH3:37])[CH:41]=1)[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])[NH:14][CH2:15][CH:16]1[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 75646CyclopropanemethanamineHCID 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 58583634N-[(1S,2S,4R)-1-Benzyl-4-(cyclopropylmethylcarbamoyl)-2-hydroxypentyl]-3-isopropoxy-5-(2-oxopyrrolidin-1-yl)benzamide

Procedure

Prepared in an analogous manner to D1 from cyclopropylmethylamine 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-6183969a8d3e45b18d34454d36c3bbf0
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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