Dicyclohexylcarbodiimide → HCID 22916736, compound

HRID 1376591Notes

Reaction equation

HRID 1376591 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:38][CH2:39][C:40]1[S:41][CH:42]=[CH:43][N:44]=1>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:38][CH2:39][C:40]1[S:41][CH:42]=[CH:43][N:44]=1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27565071,3-Thiazol-2-ylmethanamine

Product 1

HCID 22916736HCID 22916736, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

60 ml of methylene chloride was added to 3.854 g of N-tert-butoxycarbonylglycine and 2.97 g of 1-hydroxybenzotriazole. To this mixture was further added 4.54 g of dicyclohexylcarbodiimide with stirring and ice-cooling. The mixture was stirred for 2 hours with ice-cooling. To this was added 2.28 g of 2-aminomethylthiazole, and the resulting mixture was stirred for an additional 16 hours. The crystals precipitated were removed by filtration. The filtrate was washed with a 5% aqueous solution of sodium hydrogencarbonate, and dried over anhydrous magnesium sulfate. The methylene chloride was evaporated under reduced pressure. The residue was purified by flash column chromatography using silica gel, eluting with ethyl acetate to give 5.29 g (yield 97%) of 2-[(N-tert-butoxycarbonylglycyl)amino]methylthiazole.

Workup

  1. temperatureice-cooling
  2. stirringThe mixture was stirred for 2 hours with ice-
  3. temperaturecooling
  4. stirringthe resulting mixture was stirred for an additional 16 hours
  5. customThe crystals precipitated
  6. customwere removed by filtration
  7. washThe filtrate was washed with a 5% aqueous solution of sodium hydrogencarbonate
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe methylene chloride was evaporated under reduced pressure
  10. customThe residue was purified by flash column chromatography
  11. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-e823974080a8469299ac204ae1e89f52
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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