Triphenylphosphine → HCID 14835005, compound

HRID 846992Notes

Reaction equation

HRID 846992 reaction equation
[CH3:1][C:2]1[N:6]([CH:7]([CH2:10][O:11][C:12](=[O:32])[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:8]O)[N:5]=[N:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:52]=[N+]=[N-].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.[C].[Pd].C1C=CC=CC=1>[CH3:1][C:2]1[N:6]([CH:7]([CH2:10][O:11][C:12](=[O:32])[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:8][NH2:52])[N:5]=[N:4][N:3]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 24530Hydrazoic acidHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 14834986HCID 14834986, compound

Product 1

HCID 14835005HCID 14835005, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.02 g (2.25 mM) of 2-(5-methyl-1H-tetrazol-1-yl)-3-octadecylcarbamoyloxypropanol V i2, 885 mg (3.38 mM) of triphenylphosphine, and 1.9 ml (3.38 mM) of 1.8 mM benzene solution of hydrazoic acid in 50 ml of tetrahydrofurane at -50° C. is added 0.53 ml (3.38 mM) of diethyl azodicarboxylate dropwise and the mixture is raised to room temperature during 2 hr. Subsequently, 150 mg of 10% palladium carbon is added to the mixture which is stirred under hydrogen gas for 30 minutes. After 10% palladium carbon filtered off, the solvent is evaporated. The residue obtained is purified by column silica gel chromatography using ethyl acetate-chloroform/methanol (9/1) mixture as an eluent and 0.82 g (81% yield) of the title compound is obtained.

Workup

  1. filtrationAfter 10% palladium carbon filtered off
  2. customthe solvent is evaporated
  3. customThe residue obtained
  4. customis purified by column silica gel chromatography

Sources & evidence

ORD record
ord-07fe5d83f55f474fbce0bae5dae814ff
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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