Trimethylphosphine → HCID 72446128, compound

HRID 1348683Notes

Reaction equation

HRID 1348683 reaction equation
[C:1]([C:3]12[O:19][CH:18]1[CH2:17][CH:16]([C:20]([CH3:31])=[CH:21][C:22]1[N:23]=[C:24]([CH2:27][N:28]=[N+]=[N-])[S:25][CH:26]=1)[O:15][C:14](=[O:32])[CH2:13][CH:12]([OH:33])[C:11]([CH3:35])([CH3:34])[C:10](=[O:36])[CH:9]([CH3:37])[CH:8]([OH:38])[CH:7]([CH3:39])[CH2:6][CH2:5][CH2:4]2)#[N:2].CP(C)C>O1CCCC1.C(OCC)(=O)C>[C:1]([C:3]12[O:19][CH:18]1[CH2:17][CH:16]([C:20]([CH3:31])=[CH:21][C:22]1[N:23]=[C:24]([CH2:27][NH2:28])[S:25][CH:26]=1)[O:15][C:14](=[O:32])[CH2:13][CH:12]([OH:33])[C:11]([CH3:34])([CH3:35])[C:10](=[O:36])[CH:9]([CH3:37])[CH:8]([OH:38])[CH:7]([CH3:39])[CH2:6][CH2:5][CH2:4]2)#[N:2]

Participants

5

Reactant 2

HCID 68983TrimethylphosphineHCID 72446130HCID 72446130, compound

Product 1

HCID 72446128HCID 72446128, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the compound prepared in Example 5 (117 mg, 0.21 mmol) in tetrahydrofuran (2 mL) under argon was added trimethylphosphine (231 mL, 0.23 mmol, 1M in tetrahydrofuran) and the reaction was stirred at room temperature for 1 hour, then quenched with ammonium hydroxide (325 mL, 28% in water). The mixture was stirred for an additional 30 min. The volatiles were removed in vacuo and the crude material was purified (SiO2, ethyl acetate, then 1–10% MeOH/CHCl3 gradient elution). The material obtained was dissolved in ethyl acetate (20 mL) and washed twice with 20 mL portions of saturated aqueous sodium bicarbonate. The solution was dried over sodium sulfate and dried in vacuo to provide the title compound (100.5 mg, 89%) as a white solid. MS (ESI+): 534.2 (M+H)+.

Workup

  1. customquenched with ammonium hydroxide (325 mL, 28% in water)
  2. stirringThe mixture was stirred for an additional 30 min
  3. customThe volatiles were removed in vacuo
  4. customthe crude material was purified (SiO2, ethyl acetate
  5. wash1–10% MeOH/CHCl3 gradient elution)
  6. customThe material obtained
  7. washwashed twice with 20 mL portions of saturated aqueous sodium bicarbonate
  8. dry with materialThe solution was dried over sodium sulfate
  9. customdried in vacuo

Sources & evidence

ORD record
ord-a3422457d1044bcd83f9ebe1dfd07e56
Source dataset
uspto-grants-2007_05
Patent number
US07211593B2

Reaction notes

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