Ammonium Acetate → HCID 178419939, compound

HRID 2273043Notes

Reaction equation

HRID 2273043 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[N:17]=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]3[CH2:32][CH2:31][CH:30]([C:33]4[N:34]=[C:35]([C@@H:38]5[CH2:42][CH2:41][CH2:40][N:39]5C(OCC5C=CC=CC=5)=O)[NH:36][CH:37]=4)[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)[NH:19][CH:20]=1)=O)C1C=CC=CC=1.C([O-])(=O)C.[NH4+]>CC1C=CC=CC=1C>[NH:39]1[CH2:40][CH2:41][CH2:42][C@H:38]1[C:35]1[NH:36][CH:37]=[C:33]([CH:30]2[CH2:31][CH2:32][CH:27]([C:24]3[CH:25]=[CH:26][C:21]([C:18]4[NH:19][CH:20]=[C:16]([C@@H:12]5[CH2:13][CH2:14][CH2:15][NH:11]5)[N:17]=4)=[CH:22][CH:23]=3)[CH2:28][CH2:29]2)[N:34]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 178525132HCID 178525132, compound

Product 1

HCID 178419939HCID 178419939, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of A5′ (2.5 g, 3.5 mmol) in o-xylene (25 mL) in a sealed tube was added ammonium acetate (4.1 g, 53 mmol). The mixture was sealed and heated at 140° C. for 3 h and then cooled to rt. The volatile component was removed in vacuo, and the residue was partitioned between H2O and CH2Cl2, and the organic phase was dried, filtered and concentrated in vacuo. The resulting crude material was purified by silica gel column chromatography (CH2Cl2/MeOH=9/1 (v/v)) to provide A6′ as a yellow solid (250 mg, 10% yield).

Workup

  1. customThe mixture was sealed
  2. temperaturecooled to rt
  3. customThe volatile component was removed in vacuo
  4. customthe residue was partitioned between H2O and CH2Cl2
  5. customthe organic phase was dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude material was purified by silica gel column chromatography (CH2Cl2/MeOH=9/1 (v/v))

Sources & evidence

ORD record
ord-ec38b1a99d4f487593bc0951b20dca57
Source dataset
uspto-grants-2015_09
Patent number
US09120779B2

Reaction notes

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