Ethyl Acetate → HCID 69773249, compound

HRID 412137Notes

Reaction equation

HRID 412137 reaction equation
CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C.C(P(CCCC)CCCC)CCC.[CH2:30]([O:37][C:38]1[CH:39]=[C:40]([C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][C:45]=2[NH:51][C:52](=[O:62])[CH2:53][NH:54][C@@H:55]([CH2:58][CH2:59][S:60][CH3:61])[CH2:56]O)[CH:41]=[CH:42][CH:43]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CCOC(C)=O>C1COCC1>[ClH:50].[CH2:30]([O:37][C:38]1[CH:39]=[C:40]([C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][C:45]=2[N:51]2[CH2:56][C@H:55]([CH2:58][CH2:59][S:60][CH3:61])[NH:54][CH2:53][C:52]2=[O:62])[CH:41]=[CH:42][CH:43]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 13831TributylphosphineHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 70010256HCID 70010256, compound

Product 1

HCID 69773249HCID 69773249, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of di-tert-butylazodicarboxylate (733 mg, 3.2 mmol) in 7 mL of THF at 0° C. was added tributylphosphine (0.797 mL, 3.2 mmol) dropwise. After 10 minutes, a solution of the product from Step A (1.062 mg, 2.12 mmol) in 4 mL of THF was added dropwise over 15 minutes, and the reaction was allowed to warm to room temperature. After 30 minutes, the solution was poured into EtOAc, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product mixture was purified by silica gel chromatography (5-7% MeOH/CH2Cl2). The resulting product was taken up in ether, excess 1N HCl/Ether was added, the solution was concentrated in vacuo, and the resulting residue was triturated with hexane. The titled product, containing tributylphosphine oxide impurity, was used in the next reaction without further purification.

Workup

  1. waitAfter 30 minutes
  2. washwashed with sat. aq. NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product mixture was purified by silica gel chromatography (5-7% MeOH/CH2Cl2)
  7. additionexcess 1N HCl/Ether was added
  8. concentrationthe solution was concentrated in vacuo
  9. customthe resulting residue was triturated with hexane
  10. additionThe titled product, containing tributylphosphine oxide impurity
  11. customwas used in the next reaction without further purification

Sources & evidence

ORD record
ord-4c419359614349c79b311a1b4770db43
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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