2-Amino-5-methylthiazole → (2S,4R)-tert-Butyl 4-fluoro-2-(pyrazin-2-ylcarbamoyl)pyrrolidine-1-carboxylate

HRID 1961394Notes

Reaction equation

HRID 1961394 reaction equation
O[C@@H]1CN([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H](C(OC)=O)C1.CC1SC(N)=NC=1.[F:25][C@H:26]1[CH2:30][NH:29][C@H:28]([C:31]([NH:33][C:34]2[CH:39]=[N:38][CH:37]=[CH:36][N:35]=2)=[O:32])[CH2:27]1>>[F:25][C@H:26]1[CH2:30][N:29]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:28]([C:31](=[O:32])[NH:33][C:34]2[CH:39]=[N:38][CH:37]=[CH:36][N:35]=2)[CH2:27]1

Participants

4

Reactant 3

HCID 3517702-Amino-5-methylthiazoleHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl esterHCID 59436310(2S,4R)-4-Fluoro-N-(pyrazin-2-yl)pyrrolidine-2-carboxamide

Product 1

HCID 59436441(2S,4R)-tert-Butyl 4-fluoro-2-(pyrazin-2-ylcarbamoyl)pyrrolidine-1-carboxylate

Procedure

(2S,4S)-4-Hydroxy-N-(5-methylthiazol-2-yl)pyrrolidine-2-carboxamide 65A was prepared from (2S,4S)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate and 5-methylthiazol-2-amine as described for 65B. LC/MS [M+H]+: 228; Ret time (Method F): 0.55 min.

Workup

  1. custom0.55 min.

Sources & evidence

ORD record
ord-d719a12120c545f6a55ea6f1f18a9882
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

Loading…