1,2-Dichloroethane → 3-Benzothiazol-2-yl-azetidine-1-carboxylic acid tert-butyl ester

HRID 528738Notes

Reaction equation

ClCCCl.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:19]([N:26]1[CH2:29][CH:28]([C:30](O)=O)[CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[NH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[SH:40]>C(Cl)Cl>[C:22]([O:21][C:19]([N:26]1[CH2:29][CH:28]([C:30]2[S:40][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[N:33]=2)[CH2:27]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To 10 mL DCE was added 533 mg (3.7 mmol) phosphorus pentoxide and 1.57 mL (7.36 mmol) bis-trimethylsilyl ether and the mixture was heated at 80° C. for 15 minutes. 0.19 g (0.92 mmol) N-boc-azetidine-3-carboxylic acid and 108 μL (1.01 mmol) 2-aminothiophenol were added and the mixture heated at 85° C. for 20 minutes. After cooling to room temperature the mixture was diluted with 20 mL DCM and washed with 1 M Na2CO3 (2×10 mL). The organic layer was dried with Na2SO4. After filtration and evaporation of the solvent the product was purified by column chromatography (silica, hexane/EtOAc 1:1).

Workup

temperaturethe mixture heated at 85° C. for 20 minutes
temperatureAfter cooling to room temperature the mixture
washwashed with 1 M Na2CO3 (2×10 mL)
dry with materialThe organic layer was dried with Na2SO4
filtrationAfter filtration and evaporation of the solvent the product
customwas purified by column chromatography (silica, hexane/EtOAc 1:1)

Sources & evidence

ORD record: ord-14dc457f9ef24184930aed9bc7ae42b9
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346816B2

Reaction notes

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