Dicyclohexylcarbodiimide → HCID 15884739, compound

HRID 379524Notes

Reaction equation

HRID 379524 reaction equation
[CH3:1][O:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][NH:5][CH2:4]1.[C:13]([NH:20][CH2:21][C:22](O)=[O:23])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:13]([NH:20][CH2:21][C:22]([N:5]1[CH2:4][CH:3]([O:2][CH3:1])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:23])([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 12523033HCID 12523033, compound

Product 1

HCID 15884739HCID 15884739, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxy-1,2,3,4-tetrahydroisoquinoline (5.88 g, 36 mmol) in 100 mL of CH2Cl2 were added Boc-glycine (12.6 g, 72 mmol), 4-dimethylaminopyridine (8.80 g, 72 mmol), and dicyclohexyl carbodiimide (14.9 g, 72 mmol). After stirring overnight, the resulting precipitate was filtered and the filtrate was evaporated. A SiO2 chromatography (EtOAc:hexane=1:1) of the residue gave 4.9 g (43%) of the title compound.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-5d750c4afaaf43e9ba9f93875eede24c
Source dataset
uspto-grants-2001_10
Patent number
US06300316B1

Reaction notes

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