Glycine → HCID 56619281, compound

HRID 1180640Notes

Reaction equation

HRID 1180640 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[NH2:16][CH2:17][C:18]([OH:20])=[O:19].O[C:22]1[C:31]([F:32])=[C:29]([F:30])[C:27]([F:28])=[C:25]([F:26])[C:23]=1[F:24]>CN(C=O)C>[NH2:16][CH2:17][C:18]([O:20][C:22]1[C:23]([F:24])=[C:25]([F:26])[C:27]([F:28])=[C:29]([F:30])[C:31]=1[F:32])=[O:19]

Participants

5

Reactant 3

HCID 750GlycineHCID 10868DicyclohexylcarbodiimideHCID 13041Pentafluorophenol

Product 1

HCID 56619281HCID 56619281, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DCC (308 mg, 1.5 mmol) was added to a DMF solution (10 mL) of HABA-Gly-OH (299 mg, 1 mmol) and PfpOH (276 mg, 1.5 mmol) while ice cooling, and the reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (0-5% acetone/CH2Cl2) to give HABA-Gly-OPfp (46 mg, 10%) as an orange powder. 1H NMR (CDCl3) δ 9.67 (brs, 1H), 9.02 (brt, 1H), 7.8-7.7 (m, 3H), 7.6-7.5 (m, 2H), 7.23 (d, J=9 Hz, 1H), 6.86 (d, J=9 Hz, 2H), 4.67 (d, J=5 Hz, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (0-5% acetone/CH2Cl2)

Sources & evidence

ORD record
ord-68c55ef8d4db414e8281924e59d717a2
Source dataset
uspto-grants-2007_10
Patent number
US07282575B2

Reaction notes

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