2-Aminothiazole → (2S,4S)-4-Hydroxy-N-(thiazol-2-yl)pyrrolidine-2-carboxamide

HRID 1961392Notes

Reaction equation

HRID 1961392 reaction equation
[OH:1][C@@H:2]1[CH2:6][N:5](C(OC(C)(C)C)=O)[C@H:4]([C:14]([O:16]C)=O)[CH2:3]1.[NH2:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1.F[C@H]1CN(C(OC(C)(C)C)=O)[C@H](C(=O)NC2C=NC=CN=2)C1.F[C@H]1CN[C@H](C(NC2C=NC=CN=2)=O)C1>>[OH:1][C@@H:2]1[CH2:6][NH:5][C@H:4]([C:14]([NH:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[O:16])[CH2:3]1

Participants

5

Reactant 4

HCID 21552-AminothiazoleHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl esterHCID 59436310(2S,4R)-4-Fluoro-N-(pyrazin-2-yl)pyrrolidine-2-carboxamideHCID 59436441(2S,4R)-tert-Butyl 4-fluoro-2-(pyrazin-2-ylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 28943408(2S,4S)-4-Hydroxy-N-(thiazol-2-yl)pyrrolidine-2-carboxamide

Procedure

(2S,4S)-4-Hydroxy-N-(thiazol-2-yl)pyrrolidine-2-carboxamide 88A was prepared from (2S,4S)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate and 2-Amino thiazole as described for 65A and 65B. LC/MS [M+H]+: 214; Ret time (Method F): 0.35 min.

Workup

  1. custom0.35 min.

Sources & evidence

ORD record
ord-37eb98e8e4db449eb0aa76a1a2170de7
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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