Tributylphosphine → HCID 18009110, compound

HRID 987492Notes

Reaction equation

HRID 987492 reaction equation
CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C.C(P(CCCC)CCCC)CCC.[OH:30][C:31]1[CH:40]=[C:39]2[C:34]([CH:35]=[CH:36][CH:37]=[C:38]2[NH:41][C:42](=[O:55])[CH2:43][N:44]([CH2:52][CH2:53]O)[C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[CH:33][CH:32]=1>O1CCCC1>[C:48]([O:47][C:45]([N:44]1[CH2:52][CH2:53][N:41]([C:38]2[C:39]3[C:34](=[CH:33][CH:32]=[C:31]([OH:30])[CH:40]=3)[CH:35]=[CH:36][CH:37]=2)[C:42](=[O:55])[CH2:43]1)=[O:46])([CH3:49])([CH3:51])[CH3:50]

Participants

5

Reactant 3

HCID 13831Tributylphosphine2×HCID 6034084Di-tert-butyl diazene-1,2-dicarboxylate2×HCID 59116573HCID 59116573, compound

Product 1

HCID 18009110HCID 18009110, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of di-tert-butylazodicarboxylate (10.81 g, 43.2 mmol) in 60 mL of tetrahydrofuran at 0° C. was added tributylphosphine (10.76 mL, 43.2 mmol) dropwise. After 10 minutes, a solution of the crude product from Step B (ca. 28.8 mmol) in 30 mL of tetrahydrofuran was added dropwise, and the reaction was allowed to warm to room temperature. After two hours, HPLC analysis showed partial conversion. The solution was cooled to 0° C., and additional portions of tributylphosphine (3.0 mL, 18 mmol) and di-tert-butylazodicarboxylate (4.6 g, 18 mmol) were added. The reaction was warmed to room temperature, and stirred for 16 hours. The solution was concentrated in vacuo, and the resulting product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to provide the titled product as a dark brown foam, contaminated with tributylphosphine oxide impurity. This material was used in the next reaction without further purification.

Workup

  1. waitAfter two hours
  2. temperatureThe solution was cooled to 0° C.
  3. temperatureThe reaction was warmed to room temperature
  4. concentrationThe solution was concentrated in vacuo
  5. customthe resulting product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-120b00137eab45558f23cee3fad02dca
Source dataset
uspto-grants-2003_10
Patent number
US06632818B2

Reaction notes

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