Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 54064141, compound

HRID 1432899Notes

Reaction equation

HRID 1432899 reaction equation
CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[C:28]([O:32][C:33]([NH:35][CH:36]([CH2:40][O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[C:37]([OH:39])=O)=[O:34])([CH3:31])([CH3:30])[CH3:29].C(N(C(C)C)CC)(C)C.Cl.[CH3:59][NH:60][O:61][CH3:62]>C1COCC1>[C:28]([O:32][C:33](=[O:34])[NH:35][CH:36]([C:37](=[O:39])[N:60]([O:61][CH3:62])[CH3:59])[CH2:40][O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])([CH3:29])([CH3:30])[CH3:31]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 13273790HCID 13273790, compound

Product 1

HCID 54064141HCID 54064141, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-Dimethylaminopyridine (2.60 g, 21.3 mmol) and BOP reagent (18.15 g, 41.0 mmol) are added to a solution of 2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid (12.37 g, 38.7 mmol), diisopropylethylamine (8.1 mL, 46.4 mmol) and N,O-dimethylhydroxylamine hydrochloride (4.53 g, 46.4 mmol) in THF (260 mL) at RT. The resulting suspension is stirred at RT overnight then concentrated to dryness. The residue is diluted with EtOAc and washed with saturated NH4Cl, saturated NaHCO3 and brine. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to give the crude product which is purified by flash chromatography eluting with 10-30% EtOAc/Hexanes to yield the title compound (11.86 g, 30.37 mmol) as an oil. 1H NMR (CDCl3, 300 MHz) δ5.35 (bd, 1H), 4.71 (bs, 1H), 3.78-3.85 (m, 2H), 3.72 (s, 3H), 3.20 (s, 3H), 1.42 (s, 9H), 0.90 (s, 9H), 0.05 (s, 6H).

Workup

  1. concentrationthen concentrated to dryness
  2. additionThe residue is diluted with EtOAc
  3. washwashed with saturated NH4Cl, saturated NaHCO3 and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product which
  8. customis purified by flash chromatography
  9. washeluting with 10-30% EtOAc/Hexanes

Sources & evidence

ORD record
ord-849cd6e6c1f0478182bf2bb01cfa655b
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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