Benzylamine → HCID 22269501, compound

HRID 541003Notes

Reaction equation

HRID 541003 reaction equation
[N:1]([CH:4]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:5]([OH:7])=O)=[N+:2]=[N-:3].C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C.[CH2:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[N:1]([CH:4]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:5]([NH:41][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:7])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 12170845HCID 12170845, compound

Product 1

HCID 22269501HCID 22269501, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Azido-3-phenylpropanoic acid (J. T. Lundquist IV, J. C. Pelletier, Org. Lett. 2001, 3, 781-783) (112 mg, 0.588 mmol) and HOBt (108 mg, 0.705 mmol) were suspended in CH2Cl2 (2 mL), and the mixture was cooled to 0° C. under Ar(g). DIC (107 μL, 0.705 mmol) was added, and the resulting mixture was stirred for 30 min. Benzyl amine (122 μL, 1.06 mmol) was then added, and the mixture was allowed to warm to room temperature and then stirred overnight under Ar(g). The mixture was filtered, and the solvent was removed under reduced pressure. The residue was purified by silica gel flash chromatography, eluting with 15% EtOAc/hexanes, to give the required amide 2b as a white solid (117 mg, 0.418 mmol, 71% yield).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by silica gel flash chromatography
  4. washeluting with 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-4279c312411d4d9d807bedeb398ea1ea
Source dataset
uspto-grants-2014_10
Patent number
US08871916B2

Reaction notes

Loading…