Triphenylphosphine → HCID 25053656, compound

HRID 2382219Notes

Reaction equation

HRID 2382219 reaction equation
[CH2:1]([C@H:3]1[C@H:6]([CH2:7][C@H:8]([OH:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[O:5][C:4]1=[O:21])[CH3:2].[CH:22]([NH:24][CH2:25][C:26](O)=[O:27])=[O:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C(C)=CC=CC=1>[CH:22]([NH:24][CH2:25][C:26]([O:20][C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:7][C@H:6]1[C@H:3]([CH2:1][CH3:2])[C:4](=[O:21])[O:5]1)=[O:27])=[O:23]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75606FormylglycineHCID 5363146Diisopropyl azodicarboxylateHCID 57692857HCID 57692857, compound

Product 1

HCID 25053656HCID 25053656, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Prepared according to the procedure described in Example 36, above. Hydroxy β-lactone 13f (10 mg, 0.033 mmol), N-formylglycine (12.0 mg, 0.120 mmol), triphenylphosphine (26.6 mg, 0.099 mmol), and 0.5 mL of xylene were combined and the mixture was azeotroped in vacuo for 1.0 h. THF (1.4 mL) was then added followed by DIAD (21.0 μL, 0.108 mmol). After 12 hours the mixture was concentrated in vacuo, and purified by chromatography (SiO2, 10 to 30% EtOAc:hexanes) to afford β-lactone 15i (5.5 mg, 43%).

Workup

  1. customPrepared
  2. customthe mixture was azeotroped in vacuo for 1.0 h
  3. additionTHF (1.4 mL) was then added
  4. concentrationAfter 12 hours the mixture was concentrated in vacuo
  5. custompurified by chromatography (SiO2, 10 to 30% EtOAc:hexanes)

Sources & evidence

ORD record
ord-5075b92630d942c5a5f68d1d7668aeb9
Source dataset
uspto-grants-2012_09
Patent number
US08258321B2

Reaction notes

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