Triphenylphosphine → HCID 131723005, compound

HRID 2268031Notes

Reaction equation

HRID 2268031 reaction equation
[CH:1]1([CH:4]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([F:17])[CH:11]=2)O)[C:5]([OH:7])=O)[CH2:3][CH2:2]1.[CH3:18][C@@H:19]([NH-:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P([N:60]=[N+:61]=[N-:62])(C2C=CC=CC=2)=O)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:18][C@@H:19]([NH:26][C:5](=[O:7])[CH:4]([CH:1]1[CH2:2][CH2:3]1)[CH:8]([N:60]=[N+:61]=[N-:62])[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([F:17])[CH:11]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18348736HCID 18348736, compoundHCID 131723006HCID 131723006, compound

Product 1

HCID 131723005HCID 131723005, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The appropriate diastereomer of 2-cyclopropyl-3-(3,4-difluorophenyl)-3-hydroxypropionic acid N-((R)-(α-methylbenzyl)amide (1.1 g, 3.18 mmol), triphenylphosphine (1.7 g, 6.48 mmol), and diphenyl-phosphoryl azide (1.37 mL, 6.36 mmol) were combined in THF (30 mL) and cooled to −78° C. under nitrogen. Diethyl azodicarboxylate (1.2 mL, 7.63 mmol) was added and the mixture was stirred 1 hour at −78, 1 hour at 0° C. and 16 hours at ambient temperature. The reaction mixture was washed with saturated sodium bicarbonate and brine, dried the over sodium sulfate, filtered, and evaporated to dryness. The resulting oil was purified and separated by “flash” chromatography (98:2 of methylene chloride:ethyl ether). The product fractions were evaporated to dryness and the residue was reconcentrated from ethyl ether to yield the title compound as an oil.

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate and brine
  2. dry with materialdried the over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe resulting oil was purified
  6. customseparated by “flash” chromatography (98:2 of methylene chloride:ethyl ether)
  7. customThe product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-808af85c14d94f9781e1df0eb3042987
Source dataset
uspto-grants-2001_12
Patent number
US06326372B1

Reaction notes

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