Sodium Methoxide → HCID 54082073, compound

HRID 704643Notes

Reaction equation

HRID 704643 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH:14]([CH2:15][O:16]C(=O)C2C=CC=CC=2)[CH:13]1[CH2:25][O:26]C(=O)C1C=CC=CC=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH:14]([CH2:15][OH:16])[CH:13]1[CH2:25][OH:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 54428868HCID 54428868, compound

Product 1

HCID 54082073HCID 54082073, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7 N-(Benzyloxycarbonyl)-2,3-bis(benzoyloxymethyl) cyclopropylamine (0.22 g, 479 mmol) from Step F was dissolved in 5 mL of methanol. Sodium methoxide (52 mg, 95.9 mmol) was added to this solution and the reaction mixture was stirred at ambient temperature for 0.5 h. TLC analysis (on silica gel plates eluted with 10% methanol in chloroform) indicated that the starting material had been consumed in the reaction. The reaction mixture was concentrated in vacuo and the residue dissolved in water. The aqueous solution was acidified with Amberlite® IR-120(plus) acidic ion exchange resin. The resin was removed by filtration and the filtrate concentrated in vacuo. The residue was purified by column chromatography on a 2×20 cm silica gel column eluted with 5% methanol in methylene chloride. Fractions numbered 9 -14 were combined and concentrated in vacuo to give 51 mg (33.3% yield) of N-benzyloxycarbonyl 2,3-bis(hydroxymethyl) cyclopropylamine. DCI NH3MS, M/Z: 252 (M+H)+, 269 (M+NH4)+. 1H NMR (CDCl3) 1.10 (m, 1H, 1.40 (m, 1H), 1.59 (s, O-H), 2.60 (dd, 1H), 2.75 (N-H), 3.31 (ddd, 2H), 3.77 (dd, 1H), 4.00 (dd, 1 H), 5.12 (s, 2H), 7.32 (m, 5H) ppm.

Workup

  1. washTLC analysis (on silica gel plates eluted with 10% methanol in chloroform)
  2. customhad been consumed in the reaction
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue dissolved in water
  5. customThe resin was removed by filtration
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was purified by column chromatography on a 2×20 cm silica gel column
  8. washeluted with 5% methanol in methylene chloride
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1490854da65043dca940e90077a1358b
Source dataset
uspto-grants-1991_01
Patent number
US04988703

Reaction notes

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