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

HRID 1724178Notes

Reaction equation

HRID 1724178 reaction equation
[C:1]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:16][NH:17][O:18][CH3:19].C1C=CC2N(O)N=NC=2C=1.Cl.C(N=C=N)C.C(N(CC)C(C)C)(C)C>C(Cl)Cl.CCOCC>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH:10]([C:12]([N:17]([O:18][CH3:19])[CH3:16])=[O:14])[CH2:11]1)=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 21883477Ethylcarbodiimide hydrochloride

Product 1

HCID 21306970tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 980 mg (4.87 mmol) of boc-azetidine-3-carboxylic acid, 951 mg (9.75 mmol) of N,O-dimethylhydroxylamine hydrochloride, 329 mg (2.435 mmol) of HOBT and 1.87 g (9.75 mmol) of 1-[3-dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride in 30 mL of CH2Cl2 was added 2.54 mL 44.61 mmol) of N,N-diisopropylethylamine at 0° C. and it was stirred for 6 h at rt. Then the reaction mixture was poured into 100 mL of ether and washed with 20 mL of aq NaHCO3. The organic layer was dried over Na2SO4 and concentrated to afford the title compound. 1NMR(CDCl3) δ 1.46 (s, 9H), 3.23 (s, 3H), 3.62 (m, 1H), 3.68 (s, 3H), 4.07 (m, 2H), 4.09 (m, 2H).

Workup

  1. washwashed with 20 mL of aq NaHCO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9af8023dfff54667a4817c29803cb41a
Source dataset
uspto-grants-2009_02
Patent number
US07485732B2

Reaction notes

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