Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 178502719, compound

HRID 411654Notes

Reaction equation

HRID 411654 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([OH:21])=O)[CH2:15][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:23][O:24][NH:25][CH3:26].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([C:19](=[O:21])[N:25]([O:24][CH3:23])[CH3:26])[CH2:17][CH2:18]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178523389HCID 178523389, compound

Product 1

HCID 178502719HCID 178502719, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1L flask was charged with 25.02 g (85.9 mmol) trans-4-(benzyloxycarbonylamino-methy)-cyclohexanecarboxylic acid, 9,21 g (94.5 mmol) O,N-dimethylhydroxyl amine HCl, 41.8 g (94.5 mmol) BOP, 750 mL methylene chloride and 75 mL diisopropylethyl amine. The reaction mixture was then stirred under nitrogen overnight. The solution was then washed with water, 5% citric acid (2×300 mL), saturated sodium bicarbonate (2×300 mL), brine (1X 300 mL) and dried over Na2SO4 and concentrated to an oil. The oil was chromatographed on silica gel eluted with 50% ethyl acetate/50% hexanes to give 27.2 g of a clear oil that solidified on standing.

Workup

  1. washThe solution was then washed with water, 5% citric acid (2×300 mL), saturated sodium bicarbonate (2×300 mL), brine (1X 300 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to an oil
  4. customThe oil was chromatographed on silica gel
  5. washeluted with 50% ethyl acetate/50% hexanes

Sources & evidence

ORD record
ord-5b20325bf5764e1ca8e1b0c5861c8a5b
Source dataset
uspto-grants-2003_05
Patent number
US06559168B2

Reaction notes

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