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 2365598Notes

Reaction equation

HRID 2365598 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-574979bbbe1246c4a4b03ffe907094b1
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

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