3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → 3-[4-(Thiazole-2-carbonyl)-piperazin-1-yl]-azetidine-1-carboxylic acid tert-butyl ester

HRID 2365279Notes

Reaction equation

HRID 2365279 reaction equation
[N:1]1([C:7]([C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:14]([N:21]1[CH2:24][C:23](=O)[CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[B][B][B][B][B][B][B][B][B][B]>CO>[C:17]([O:16][C:14]([N:21]1[CH2:24][CH:23]([N:4]2[CH2:3][CH2:2][N:1]([C:7]([C:9]3[S:10][CH:11]=[CH:12][N:13]=3)=[O:8])[CH2:6][CH2:5]2)[CH2:22]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 21641598Piperazin-1-yl(thiazol-2-yl)methanoneHCID 178419135HCID 178419135, compound

Product 1

HCID 596260133-[4-(Thiazole-2-carbonyl)-piperazin-1-yl]-azetidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 7b (6.1 g, 0.031 mol) and (5.1 g, 0.03 mol) compound 4a in MeOH (30 mL) was stirred for 15 min. Decaborane (1 g, 0.008 mol) was added and the reaction was stirred for 18 h. The solvent was evaporated in vacuo. The residue was used without further purification for the next step. MS m/z (M+H+) 353.1.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was used without further purification for the next step

Sources & evidence

ORD record
ord-8bbb1106e66441a5930fcc5b0cca3be3
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

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