1-Hydroxybenzotriazole → tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate

HRID 1972743Notes

Reaction equation

HRID 1972743 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C.Cl.[CH3:47][NH:48][O:49][CH3:50]>C1COCC1>[CH3:50][O:49][N:48]([CH3:47])[C:12]([CH:10]1[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:11]1)=[O:14]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27559811-Boc-Azetidine-3-carboxylic acid

Product 1

HCID 21306970tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (2.00 g, 9.94 mmol) in THF (50 mL) was added EDCl (2.10 g, 10.93 mmol), HOBt (1.48 g, 10.93 mmol), and N,N-diisopropylethylamine (5.19 mL, 29.82 mmol). The mixture was stirred at rt for 15 min. N,O-dimethylhydroxylamine hydrochloride (1.16 g, 11.93 mmol), was added and stirring continued for 64 h. The crude reaction was purified via ISCO® chromatography using 3:1 ethyl/hexanes to afford 2.4 g (99%) of the desired product, which was used without further characterization.

Workup

  1. stirringstirring
  2. waitcontinued for 64 h
  3. customThe crude reaction
  4. customwas purified via ISCO® chromatography

Sources & evidence

ORD record
ord-b4b349dc9b0e4ad5add8512f45dc6877
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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