Ammonium Hydroxide → HCID 18650089, compound

HRID 1612808Notes

Reaction equation

HRID 1612808 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[O:12][C@H:11]1[C:13]([O:15]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+:17].[OH-]>CO.C(Cl)(Cl)Cl>[CH2:1]([O:8][CH2:9][C@H:10]1[O:12][C@H:11]1[C:13]([NH2:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 15138852HCID 15138852, compound

Product 1

HCID 18650089HCID 18650089, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent2×

Procedure

To a solution of 50 mg of methyl (2R-cis)-3-(benzyloxymethyl)oxirane carboxylate in 3 ml of MeOH was added 1 ml of concentrated NH4OH with rapid stirring. The mixture was allowed to stir for two days. The reaction was then diluted with 20 ml of CHCl3 and the organic layer separated and washed three times with 10 ml of 0.1N HCl. The combined organic layers were dried over MgSO4, filtered and evaporated to yield a pale yellow residue. Flash chromatography (7 mm column, 5% MeOH: CHCl3) afforded 24.2 mg of a clear oil which solidified upon standing. 1H NMR (CDCl3) 7.4-7.2 (m, 5), 6.08 (br, 1), 5.64 (br, 1), 4.58 (dd, 2, J=12, 15 Hz), 3.8 (m, 1), 3.5-3.4 (m, 3). Mass Spectra: EI: M-41 (--CONH2) Calc. 163.0758, Found 163.0745.

Workup

  1. customthe organic layer separated
  2. washwashed three times with 10 ml of 0.1N HCl
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto yield a pale yellow residue

Sources & evidence

ORD record
ord-b8224e4d1780477ab8703f1f67c39202
Source dataset
uspto-grants-1993_03
Patent number
US05190969

Reaction notes

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