Triethylamine → HCID 87824103, compound

HRID 852871Notes

Reaction equation

HRID 852871 reaction equation
[CH3:1][O:2][P:3]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(Cl)=[O:4].[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C@@H:31]([NH:34][C:35](=[O:48])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:32][OH:33])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(CC)CC>C1COCC1>[CH3:1][O:2][P@@:3]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:4])[O:33][CH2:32][CH:31]([NH:34][C:35](=[O:48])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[CH2:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 58929457HCID 58929457, compoundHCID 91104057HCID 91104057, compound

Product 1

HCID 87824103HCID 87824103, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

With ice-bath cooling, phosphonochloridate 53 (123 mg, 0.50 mmol) in dry THF (1.0 mL) was added dropwise to a solution of 55 (100 mg, 0.22 mmol) and Et3N (94 μL, 0.67 mmol) in dry THF (0.5 mL). After 10 min, the mixture was warmed to rt and stirred overnight. The Et3N.HCl precipitate was removed by filtration and the solvent evaporated under reduced pressure. The residue was dissolved in EtOAc, washed successively with KHSO4 (5% w/v), saturated NaHCO3, water, brine and dried (MgSO4). The solvent was removed in vacuo and the residue (209 mg) was purified on a C-18 reverse phase column to provide a diastereomeric mixture of 56a,b (82 mg, 56%) as an oil.

Workup

  1. temperatureWith ice-bath cooling
  2. customThe Et3N.HCl precipitate was removed by filtration
  3. customthe solvent evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed successively with KHSO4 (5% w/v), saturated NaHCO3, water, brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo
  8. customthe residue (209 mg) was purified on a C-18 reverse phase column
  9. customto provide
  10. additiona diastereomeric mixture of 56a,b (82 mg, 56%) as an oil

Sources & evidence

ORD record
ord-1aa2d2c7cc934a1cb064ea0f8064094a
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

Loading…