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 1852579Notes

Reaction equation

HRID 1852579 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-73d9eceab1d649c39eed819193e85632
Source dataset
uspto-grants-2015_02
Patent number
US08962607B2

Reaction notes

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