Ammonium Acetate → HCID 68863412, compound

HRID 1725885Notes

Reaction equation

HRID 1725885 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:21]=[CH:20][C:19]3[CH2:18][CH2:17][CH2:16][C:15](=O)[C:14]=3[C:13]=2[C:23]([OH:25])=[O:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[BH3-]C#[N:28].[Na+].C([O-])(=O)C.[NH4+]>CO>[NH2:28][CH:15]1[C:14]2[C:13]([C:23]([OH:25])=[O:24])=[C:12]([NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH:21]=[CH:20][C:19]=2[CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 68864168HCID 68864168, compound

Product 1

HCID 68863412HCID 68863412, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Example 103B (20 mg, 0.055 mmol), NaCNBH3 (17.2 mg, 0.275 mmol), and ammonium acetate (42 mg, 0.55 mmol) in methanol (5 mL) was heated to reflux overnight and concentrated. The concentrate was purified by reverse-phase HPLC to provide the desired product. MS (ESI) m/e 363 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 8.4 (br s, 2H), 7.66 (m, 2H), 7.36 (m, 2H), 7.25 (d, 1H), 7.14 (d, 1H), 4.42 (br s, 1H), 2.65 (m, 2H), 2.06 (m, 2H), 1.68 (m, 2H).

Workup

  1. temperatureto reflux overnight
  2. concentrationconcentrated
  3. customThe concentrate was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-78d1e91094034cb7a412c727739b9a5a
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

Loading…