Oxirane, ((phenylmethoxy)methyl)-, (S)- (9CI) → HCID 68527184, compound

HRID 237879Notes

Reaction equation

HRID 237879 reaction equation
[N:1]#[C:2][NH2:3].[Na].[CH2:5]([O:12][CH2:13][C@@H:14]1[CH2:16][O:15]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CO>[CH2:5]([O:12][CH2:13][C@H:14]1[O:15][C:2]([NH2:3])=[N:1][CH2:16]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 146296Oxirane, ((phenylmethoxy)methyl)-, (S)- (9CI)HCID 57375518Cyanamidnatrium

Product 1

HCID 68527184HCID 68527184, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a vigorously stirred solution of sodium hydrogen cyanamide (1.95 g, 30.4 mmol) in methanol (30.5 mL) was added dropwise (S)-2-benzyloxymethyl-oxirane (5 g, 30.4 mmol) in methanol. The reaction mixture was stirred at room temperature overnight after which the reaction mixture was concentrated to remove methanol. Ethyl acetate was added (150 mL) along with 50 ml of water. The contents were transferred to a separatory funnel, the organic layer was removed, dried over Na2SO4 and concentrated under vacuum to give 6.01 g (96%) of the title compound.

Workup

  1. concentrationwas concentrated
  2. customto remove methanol
  3. additionEthyl acetate was added (150 mL) along with 50 ml of water
  4. customThe contents were transferred to a separatory funnel
  5. customthe organic layer was removed
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-babb6067cdf046538ca41461844b2546
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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