Benzylamine → HCID 18653518, compound

HRID 1728374Notes

Reaction equation

HRID 1728374 reaction equation
[CH3:1][C:2]([CH3:27])([O:4][C:5]([C@H:7]([NH:18][C@H:19]([C:24](O)=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:8][CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])=[O:6])[CH3:3].[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.OC1C2N=NNC=2C=CC=1>CN(C=O)C>[CH3:3][C:2]([O:4][C:5](=[O:6])[C@H:7]([NH:18][C@H:19]([C:24]([NH:35][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:25])[CH2:20][CH:21]([CH3:22])[CH3:23])[CH2:8][CH2:9][O:10][Si:11]([C:14]([CH3:16])([CH3:17])[CH3:15])([CH3:13])[CH3:12])([CH3:1])[CH3:27]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 10069761HCID 10069761, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 18653518HCID 18653518, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

11.4 g of N-[(R)-1-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-L-leucine, prepared as in Example I, 3.64 g benzylamine, and 4.59 g hydroxybenzotriazole in 150 mL DMF was sparged with nitrogen for 10 min. 7.02 g of d icyclohexylcarbodiimide in 50 mL DMF was added dropwise at 0° C. The mixture was stirred for 15 h at 23° C., filtered, and the solvents were removed by evaporation. The residue was purified by silica chromatography using 80% hexane-ethyl acetate as eluent to give the title compound as a brown oil; 8.8 g.

Workup

  1. customwas sparged with nitrogen for 10 min
  2. addition7.02 g of d icyclohexylcarbodiimide in 50 mL DMF was added dropwise at 0° C
  3. filtrationfiltered
  4. customthe solvents were removed by evaporation
  5. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-eea44e5ba78d4b779b31f769365e3279
Source dataset
uspto-grants-1994_07
Patent number
US05326760

Reaction notes

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