Benzylamine → HCID 22252169, compound

HRID 1953527Notes

Reaction equation

HRID 1953527 reaction equation
[O:1]=[C:2]([N:14]1[CH2:26][CH2:25][C:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]=2[CH:15]1[C:27]1[CH:32]=[CH:31][C:30]2[O:33][CH2:34][O:35][C:29]=2[CH:28]=1)/[CH:3]=[CH:4]/[C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1.[CH2:36]([NH2:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CCN(CC)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[CH2:36]([NH:43][C:9](=[O:10])[C:8]1[CH:7]=[CH:6][C:5](/[CH:4]=[CH:3]/[C:2](=[O:1])[N:14]2[CH2:26][CH2:25][C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][C:16]=3[CH:15]2[C:27]2[CH:32]=[CH:31][C:30]3[O:33][CH2:34][O:35][C:29]=3[CH:28]=2)=[CH:13][CH:12]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 15887798HCID 15887798, compound

Product 1

HCID 22252169HCID 22252169, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This product was prepared by stirring a solution of Example 31 (0.2 g, 0.43 mmol) in 50 mL of THF with benzylamine (0.5 mL, 9 equiv.), Et3N (1 mL) and diphenylphosphoryl azide (0.5 mL). After two days the reaction mixture was concentrated in vacuo. The residue was taken up in 100 mL of DCM and washed with 3×50 mL of water. Drying over Na2SO4 and evaporation of the solvent gave a residue which was purified via flash chromatography with cyclohexane and Et2O. Evaporation in vacuo and recrystallization from EtOH gave the title compound (0.03 g, 13%) as white crystals.

Workup

  1. customThis product was prepared
  2. concentrationAfter two days the reaction mixture was concentrated in vacuo
  3. washwashed with 3×50 mL of water
  4. dry with materialDrying over Na2SO4 and evaporation of the solvent
  5. customgave a residue which
  6. customwas purified via flash chromatography with cyclohexane and Et2O
  7. customEvaporation
  8. customin vacuo and recrystallization from EtOH

Sources & evidence

ORD record
ord-b0df87b9ad8242b3affb39487d7e2980
Source dataset
uspto-grants-2000_09
Patent number
US06117881

Reaction notes

Loading…