Ammonium Acetate → HCID 15221160, compound

HRID 1708582Notes

Reaction equation

HRID 1708582 reaction equation
[CH3:1][C@H:2]1[C@H:7]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@@H:4]([OH:21])[CH2:3]1)[C@:16]1([CH3:17])[CH:11](CCC[CH2:15]1)[CH2:10][CH2:9]3.[C:22]([O-:25])(=O)[CH3:23].[NH4+:26]>C(O)CO>[CH3:1][C@H:2]1[C@H:7]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@@H:4]([OH:21])[CH2:3]1)[C@:16]1([CH3:17])[C:11]([NH:26][C:22](=[O:25])[CH2:23][CH2:15]1)=[CH:10][CH2:9]3

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 67651641HCID 67651641, compound

Product 1

HCID 15221160HCID 15221160, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

The secoacid (10) (1.24 g, 3.7 mmol) was mixed with ammonium acetate (1.7 g, 22.2 mmol) and ethylene glycol (23 mL) in a 50 mL round bottomed flask fitted with a stirrer bar and a rubber septum. The flask was heated under nitrogen to 1800 slowly over 40 minutes at kept there for 2 h. The mixture was cooled to 70° and the solution poured into 200 mL of ice water. The product precipitated out, was filtered and washed with water. The precipitate was dried under reduced pressure. Recovered product: (0.72 g, 2.2 mmol, 61%) δH (CDCl3) 0.90 (s, 3H), 0.99 (d, J=7 Hz,), 1.11 (s, 3H), 3.60 (t, J=7 Hz, 1H), 4.81 (m, 1H), 7.37(bs, 1H).

Workup

  1. customfitted with a stirrer bar
  2. temperatureThe flask was heated under nitrogen to 1800 slowly over 40 minutes
  3. temperatureThe mixture was cooled to 70°
  4. customThe product precipitated out
  5. filtrationwas filtered
  6. washwashed with water
  7. customThe precipitate was dried under reduced pressure

Sources & evidence

ORD record
ord-7e55450d8e25469185e417a1eff4058a
Source dataset
uspto-grants-1994_10
Patent number
US05359071

Reaction notes

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