Triphenylphosphine → HCID 12018747, compound

HRID 1860631Notes

Reaction equation

HRID 1860631 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:16])([CH3:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.O[CH2:18][CH2:19][C:20]1[N:25]=[C:24]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:23]=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:29]([O:28][C:27]([NH:26][C:24]1[N:25]=[C:20]([CH2:19][CH2:18][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([CH3:16])([CH3:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:7]=2)[CH:21]=[CH:22][CH:23]=1)=[O:33])([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 18624193HCID 18624193, compoundHCID 22347558HCID 22347558, compound

Product 1

HCID 12018747HCID 12018747, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

To a stirred solution of the product of STEP 4 (0.45 g), the product of STEP 6 (0.723 g), triphenyl phosphine (0.80 g, Aldrich) in THF (10 mL) at −78° C. was added diisopropyl azodicarboxylate (Aldrich, 0.63 mL) over 3 minutes. The mixture was stirred at −78° C. for 3 hours and at 22° C. for 16 hours. The mixture was concentrated in vacuo and the residue was chromatographed over silica gel using 20% ethyl acetate in hexane as eluant. The fractions containing the desired product were pooled and concentrated to provide the above product as a thick gum.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was chromatographed over silica gel using 20% ethyl acetate in hexane as eluant
  3. additionThe fractions containing the desired product
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2ebe05f11f304585889390d5039474a7
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

Loading…