Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 66988034, compound

HRID 1945566Notes

Reaction equation

HRID 1945566 reaction equation
Cl.CN[O:4][CH3:5].[CH:6]([N:9](C(C)C)CC)(C)C.[C:15]([O:19][C:20]([N:22]1[CH2:25][CH:24]([C:26]([OH:28])=O)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].Cl.CN(C)CCCN=C=NCC>ClCCl>[C:15]([O:19][C:20]([N:22]1[CH2:23][CH:24]([C:26](=[O:28])[NH:9][CH2:6][O:4][CH3:5])[CH2:25]1)=[O:21])([CH3:16])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 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 66988034HCID 66988034, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of N,O-dimethylhydroxylamine hydrochloride (773 mg, 7.93 mmol) and diisopropylethylamine (1.38 mL, 7.93 mmol) in dichloromethane (5 mL) was added to a mixture of azetidine-1,3-dicarboxylic acid mono-tert-butyl ester (1.0 g, 5.30 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.27 g, 6.63 mmol) in dichloromethane (10 mL). The resulting reaction mixture was stirred at RT under nitrogen atmosphere for 16 h. The organic phase was washed with water (1×25 mL), 10% aqueous citric acid solution (2×25 mL), brine (1×30 mL), and dried over sodium sulphate. The solvents were reduced in vacuo to afford the title compound as pale yellow oil (1.06 g, 82%). 1H NMR (400 MHz, CDCl3): δ 4.14 (2 H, m), 4.05 (2 H, t, J=8.72 Hz), 3.66 (4 H, s), 3.20 (3 H, s), 1.43 (9 H, s).

Workup

  1. customThe resulting reaction mixture
  2. washThe organic phase was washed with water (1×25 mL), 10% aqueous citric acid solution (2×25 mL), brine (1×30 mL)
  3. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-c8f34206004f4b91a166077536d7dde9
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

Loading…