Triphenylphosphine → HCID 13036861, compound

HRID 1156742Notes

Reaction equation

HRID 1156742 reaction equation
N#N.[C:3]1([CH2:9][C:10]([NH:12][C@H:13]([C:16]([NH:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:17])[CH2:14]O)=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:3]1([CH2:9][C:10]([NH:12][C@H:13]2[CH2:14][N:18]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:16]2=[O:17])=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86738444HCID 86738444, compound

Product 1

HCID 13036861HCID 13036861, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
26 °C

Procedure

To a cold solution (0° C.) of N2 -(phenylacetyl)-N-[(phenylmethyl)oxy]-L-serinamide (6.88 g) in distilled tetrahydrofuran (300 ml), under nitrogen, is added triphenylphosphine (11.20 g) followed by diethylazodicarboxylate (6.60 ml). The solution is allowed to warm to 26° C. and stirred for twelve hours. After removal of solvent under reduced pressure the resulting residue is applied to a silica gel column (eluant ether/hexane→ether). Combination of fractions gives two batches; 1.0 g (pure) and 2.5 g (ca. 60% pure) (total yield ca. 2.2 g). The pure material is recrystallized from ethyl acetate/hexane to give solids; melting point 130°-131° C.

Workup

  1. customAfter removal of solvent under reduced pressure the resulting residue
  2. customCombination of fractions gives two batches
  3. customThe pure material is recrystallized from ethyl acetate/hexane
  4. customto give solids

Sources & evidence

ORD record
ord-677da9e645fb411e9835dfadcb9c3d05
Source dataset
uspto-grants-1982_06
Patent number
US04337197

Reaction notes

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