Water → HCID 18672401, compound

HRID 1058267Notes

Reaction equation

HRID 1058267 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:12]=1[CH2:13][N:14]=[N+]=[N-])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:12]=1[CH2:13][NH2:14])[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 18672376HCID 18672376, compound

Product 1

HCID 18672401HCID 18672401, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution 2-(1-tert-butyloxycarbonylaminoethyl)-5-chlorobenzylazide from the previous step (0.28 g, 0.90 mmol) in THF (10.0 mL) and water (1 mL) at ambient temperature was added Ph3P (0.29 mg, 1.1 mmol). The mixture was refluxed for 3 h. The reaction was partitioned between Et2O and diluted 1N HCl. The Et2O layer was removed, and the aqueous layer basicified with saturated NaHCO3 solution. The aqueous layer was extracted with Et2O which was separated, dried over anhydrous Na2SO4, and filtered. The filtrate solvent was removed under reduced pressure. 2-(1-(tert-butyloxycarbonylamino)ethyl)-5-chlorobenzylamine was obtained as a pink oil (0.205 g; HPLC RT=2.76 min, method A; 1H NMR, 400 MHz, CDCl3, 7.33 ppm (s, 1H), 7.22 ppm (dd, 2H), 5.2 ppm (br s, 1H), 5.0 ppm (br s, 1H), 4.0 ppm (d, 1H), 3.85 ppm (d, 1H), 1.7 (br s, 1H), 1.4 ppm (s, 12H)).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. customThe reaction was partitioned between Et2O
  3. additiondiluted 1N HCl
  4. customThe Et2O layer was removed
  5. extractionThe aqueous layer was extracted with Et2O which
  6. customwas separated
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customThe filtrate solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5a82901468c043bd8251368ff500faad
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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