Potassium Carbonate → Methyl 5-(((1-(tert-butoxycarbonyl)azetidin-3-yl)amino)methyl)thiazole-4-carboxylate

HRID 409889Notes

Reaction equation

HRID 409889 reaction equation
Br[CH2:2][C:3]1[S:7][CH:6]=[N:5][C:4]=1[C:8]([O:10][CH3:11])=[O:9].[C:12]([N:19]1[CH2:22][CH:21]([NH2:23])[CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+]>C1COCC1.C(Cl)Cl>[C:15]([O:14][C:12]([N:19]1[CH2:22][CH:21]([NH:23][CH2:2][C:3]2[S:7][CH:6]=[N:5][C:4]=2[C:8]([O:10][CH3:11])=[O:9])[CH2:20]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 66601492Methyl 5-(bromomethyl)thiazole-4-carboxylate

Product 1

HCID 66601525Methyl 5-(((1-(tert-butoxycarbonyl)azetidin-3-yl)amino)methyl)thiazole-4-carboxylateYield 60.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of compound 3b (250 mg, 1.06 mmol), 1-Boc-3-aminoazetidine 1a (310 mg, 1.80 mmol), and K2CO3 (248 mg, 1.80 mmol) in THF (12 mL) was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and diluted with CH2Cl2. The resulting solution was washed with aq. NaHCO3, dried over Na2SO4, and concentrated. Purification by flash column chromatography (silica gel, 3% MeOH/CH2Cl2) gave compound 3c (210 mg).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h
  3. washThe resulting solution was washed with aq. NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (silica gel, 3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7ff89c48a55b4992bde5456e47ebe3ce
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

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