Ammonia → HCID 22843776, compound

HRID 1195415Notes

Reaction equation

HRID 1195415 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C@H:21]2[O:23][C@@H:22]2[C:24]([O:26]C2C=CC3C(=CC=CC=3)C=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:37]>CO>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C@H:21]2[O:23][C@@H:22]2[C:24]([NH2:37])=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54222053HCID 54222053, compound

Product 1

HCID 22843776HCID 22843776, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester of Example 6b, (2S-trans)-2-naphthalenyl 3-[2-(8-phenyloctyl)phenyl]oxiranecarboxylate (2.03 g, 4.2 mmol), in methanol (21 mL) was cooled to 5° C. and a solution of ammonia saturated methanol (20 mL) was added dropwise. After stirring for 5 h at 10°-15° C., the solution was evaporated. The residue was dissolved in toluene and evaporated to a solid. The solid was dissolved in toluene and washed with water, NaOH (10%), water, and finally brine. After drying (MgSO4) and evaporation, the residue was dissolved in boiling hexane CH2Cl2 (8:2), filtered and allowed to stand at 20° C. for 4 h. The solid was collected and dried (0.1 mm Hg, 25° C.) to yield the titled oxiranecarboxamide 1.11 g (76%): mp 80°-82° C.; [α]D -8.3° (c 1, CH2Cl2); HPLC RT 5.48 min (2S-enantiomer); 9.99 min (2R-enantiomer) (Bakerbond Chiracel OC; 25 cm×4.6 mm; hexane:isopropanol, 1:1; 1.0 mL/min; UV detection at 211 nm); HPLC showed the product at >99% e.e. Anal. Calcd for C23H29O2N: C, 78.59; H, 8.32; N, 3.99. Found: C, 78.35; H, 8.34; N, 3.90.

Workup

  1. customthe solution was evaporated
  2. dissolutionThe residue was dissolved in toluene
  3. customevaporated to a solid
  4. dissolutionThe solid was dissolved in toluene
  5. washwashed with water, NaOH (10%), water, and finally brine
  6. customAfter drying
  7. custom(MgSO4) and evaporation
  8. dissolutionthe residue was dissolved
  9. filtrationfiltered
  10. waitto stand at 20° C. for 4 h
  11. customThe solid was collected
  12. customdried (0.1 mm Hg, 25° C.)

Sources & evidence

ORD record
ord-9d60ee32580c4476818d8466f4e132c6
Source dataset
uspto-grants-1992_05
Patent number
US05110959

Reaction notes

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