Ammonium Chloride → HCID 178527575, compound

HRID 23607Notes

Reaction equation

HRID 23607 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9]([NH:12][C@H:13]2[CH2:18][CH2:17][C@@H:16]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:20]=3[OH:26])[CH2:15][CH2:14]2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH4+].[Cl-].[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C=O)C>[OH:26][C:20]1[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:19]=1[C@@H:16]1[CH2:15][CH2:14][C@H:13]([NH:12][S:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]3[NH:31][N:30]=[N:29][N:2]=3)[CH:4]=2)(=[O:11])=[O:10])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 178509886HCID 178509886, compound

Product 1

HCID 178527575HCID 178527575, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A solution of Example 9 (20 mg, 54 μmol) in DMF (2 ml) was treated with NH4Cl (17 mg, 323 μmol) and NaN3 (21 mg, 323 μmol). The mixture was heated under reflux for 6 hr, then stirred for 18 hr at 20° C., before being partitioned between EtOAc (30 ml) and H2O (5 ml). The aqueous phase was extracted with EtOAc (3×15 ml) and the combined organic extracts were washed with brine (30 ml) and dried (MgSO4). Filtration, solvent evaporation under reduced pressure, and FCC (EtOH-EtOAc, 1:3) afforded the title compound (16 mg, 72%) as a pale yellow solid. δH ((CD3)2CO) 1.30-1.88 (m, 8H), 2.60-2.71 (m, 1H), 3.62-3.69 (m, 1H), 4.23-4.30 (m, 1H), 6.20 (dd, 1H), 6.44 (d, 1H), 6.50 (d, 1H), 6.87 (d, 1H), 7.55 (t, 1H), 7.63-7.68-(m, 1H), 7.72-7.76 (m, 1H), 7.80 (d, 1H), 8.30 (d, 1H), 8.73 (s, 1H); m/z (ES−) 414 [M−H]−.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 hr
  3. custombefore being partitioned between EtOAc (30 ml) and H2O (5 ml)
  4. extractionThe aqueous phase was extracted with EtOAc (3×15 ml)
  5. washthe combined organic extracts were washed with brine (30 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration, solvent evaporation under reduced pressure, and FCC (EtOH-EtOAc, 1:3)

Sources & evidence

ORD record
ord-b20c561bef6045a58cfbff82992c8ef2
Source dataset
uspto-grants-2005_02
Patent number
US06852747B2

Reaction notes

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