Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86677917, compound

HRID 245908Notes

Reaction equation

HRID 245908 reaction equation
[C:1]([NH:8][C@@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.CN[O:17][CH3:18].[CH:19]([N:22](CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:4]([O:3][C:1](=[O:2])[NH:8][C@@H:9]([C:11](=[O:13])[NH:22][CH2:19][O:17][CH3:18])[CH3:10])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 637606BOC-D-alanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86677917HCID 86677917, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A round-bottomed flask was charged with Boc-D-alanine (1.0 g, 5.29 mmol) and N,O-dimethylhydroxylamine hydrochloride (670 mg, 6.87 mmol). DMF (12 ml) was added followed by N,N-diisopropylethylamine (2.4 ml, 13.7 mmol) and HATU (2.21 g, 5.81 mmol). The yellow suspension was stirred at room temperature for 48 h. The reaction mixture was quenched with water and petroleum ether was added. The resulting suspension was filtered, washed with water and petroleum ether and dried under high vacuum to afford 1.05 g (85%) of [(R)-1-(methoxymethyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester as a white powder.

Workup

  1. customThe reaction mixture was quenched with water and petroleum ether
  2. additionwas added
  3. filtrationThe resulting suspension was filtered
  4. washwashed with water and petroleum ether
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-9ee13754ec744869acdc024762d82ce9
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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