Triphenylphosphine → HCID 68770630, compound

HRID 1174182Notes

Reaction equation

HRID 1174182 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH2:4][N:3]1[C@@H:8]([C@@H:16]([CH3:19])[CH2:17][CH3:18])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH3:20][C:21]1[N:26]=[C:25]([CH2:27]O)[CH:24]=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl.O>[CH3:19][C@@H:16]([CH2:17][CH3:18])[C@H:8]([N:3]1[CH2:4][C:5](=[O:7])[N:6]([CH2:27][C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:20])[N:26]=2)[C:2]1=[O:1])[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 707366-Methyl-2-pyridylmethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66891458tert-butyl(2S,3S)-2-(2,4-dioxo-1-imidazolidinyl)-3-methylpentanoate

Product 1

HCID 68770630HCID 68770630, compoundYield 103.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution containing the product from Example 36C (0.107 g, 0.396 mmol) in dichloromethane (2 mL) at 0° C. was treated with 6-methyl-2-pyridinemethanol (0.053 g, 0.435 mmol), triphenylphosphine (0.135 g, 0.515 mmol), followed by diethyl azodicarboxylate (0.080 mL, 0.515 mmol), stirred at 25° C. for 16 hours. Water (2 mL) was added and the reaction was stirred for 2 hours at 25° C. The reaction mixture was partitioned between dichloromethane and water, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-30% ethyl acetate/dichloromethane to give the title compound (0.154 g, 94% yield).

Workup

  1. stirringthe reaction was stirred for 2 hours at 25° C
  2. customThe reaction mixture was partitioned between dichloromethane and water
  3. washthe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with 0-30% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-f64beb3650fa48d79cc62323121808f2
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

Loading…