Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 178502729, compound

HRID 1422929Notes

Reaction equation

HRID 1422929 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[CH2:6]([O:13][C:14]([NH:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23]([OH:25])=O)[CH2:19][CH2:18]1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH2:6]([O:13][C:14](=[O:15])[NH:16][C@H:17]1[CH2:18][CH2:19][C@H:20]([C:23](=[O:25])[N:3]([O:4][CH3:5])[CH3:2])[CH2:21][CH2:22]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178523781HCID 178523781, compound

Product 1

HCID 178502729HCID 178502729, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,O-dimethyl-hydroxylamine hydrochloride (10 mg, 0.10 mmol, 1.2 equivalent) is added at room temperature to a stirred solution of trans-4-benzyloxycarbonylamino-cyclohexanecarboxylic acid (23 mg, 0.08 mmol, 1.0 eq) in N,N-dimethylformamide (5 mL), followed by O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (63 mg, 0.16 mmol, 2.0 eq) and sodium hydrogen carbonate (15 mg, 0.18 mmol, 2.2 eq). After 12 hours stirring at room temperature, solvent is evaporated and the residue is extracted with ethyl acetate (3×10 mL) and a saturated ammonium chloride aqueous solution (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 2:1, v/v) to afford [trans-4-(methoxy-methyl-carbamoyl)-cyclohexyl]-carbamic acid benzyl ester as a colorless solid (8 mg, 30% yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with ethyl acetate (3×10 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue that
  7. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-0d7cb3fe428f46f18f76fed30046bf75
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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