Triphenylphosphine → HCID 58399308, compound

HRID 1927268Notes

Reaction equation

HRID 1927268 reaction equation
[O:1]([C:8]1[S:12][C:11]([CH2:13]O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:15]1[NH:16][N:17]=[N:18][C:19]=1[C:20]1[C:21]([NH2:26])=[N:22][CH:23]=[CH:24][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH-].[Na+]>O.CO.C1COCC1>[O:1]([C:8]1[S:12][C:11]([CH2:13][N:16]2[N:17]=[N:18][C:19]([C:20]3[C:21]([NH2:26])=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 131016573-(2H-Tetrazol-5-yl)pyridin-2-amineHCID 54394866HCID 54394866, compound

Product 1

HCID 58399308HCID 58399308, compoundYield 11.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of THF (5 mL) and (5-phenoxy-thiophen-2-yl)-methanol (100 mg) described in Manufacturing Example 46-1, 3-(2H-tetrazol-5-yl)-pyridin-2-ylamine (79 mg) described in Manufacturing Example 5-1, and triphenylphosphine (250 mg) was added diethyl azodicarboxylate (170 mg, 40% toluene solution) at room temperature, which was stirred for 20 minutes. Water was added to the reaction solution, which was then extracted with ethyl acetate. The solvent was evaporated from the organic layer under a reduced pressure and purified by silica gel chromatography (hexane:ethyl acetate=2:1, then 1:1), after which was purified by NH silica gel column chromatography (heptane:ethyl acetate=2:1). The solvent was evaporated under a reduced pressure from the organic layer thus obtained, methanol and 2N aqueous sodium hydroxide were added to the residue, which was stirred for 20 minutes at 80° C. Water was added to the reaction solution, which was extracted with ethyl acetate, and the organic layer was washed three times with water. The solvent was evaporated under a reduced pressure and the organic layer was purified by NH silica gel chromatography (ethyl acetate) to obtain the titled compound (20 mg).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. customThe solvent was evaporated from the organic layer under a reduced pressure
  3. custompurified by silica gel chromatography (hexane
  4. customethyl acetate=2:1, then 1:1), after which was purified by NH silica gel column chromatography (heptane:ethyl acetate=2:1)
  5. customThe solvent was evaporated under a reduced pressure from the organic layer
  6. customthus obtained
  7. stirringwas stirred for 20 minutes at 80° C
  8. extractionwas extracted with ethyl acetate
  9. washthe organic layer was washed three times with water
  10. customThe solvent was evaporated under a reduced pressure
  11. customthe organic layer was purified by NH silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-d96e94b0ccea413e9385df8760f2dde6
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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