Dicyclohexylcarbodiimide → Methyl L-prolinate

HRID 2225893Notes

Reaction equation

HRID 2225893 reaction equation
S(C1C=CC=CC=1C(NC1[N:11]([C@H:15]([CH2:19][CH2:20][CH2:21]CCC)[C:16]([OH:18])=[O:17])C=CN=1)=O)(O)(=O)=O.O[C:30]1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH3:30][O:18][C:16](=[O:17])[C@@H:15]1[CH2:19][CH2:20][CH2:21][NH:11]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 86748103HCID 86748103, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 853477Methyl L-prolinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the above amine in 10 mL of anhydrous DMF was added (R)-[(2-sulfobenzoyl)amino-1H-imidazol-1-yl]-octanoic acid (1.00 g, 2.45 mmol) and hydroxybenzotriazole (0.37 g, 2.77 mmol). This mixture was cooled to 0° C., and then treated with dicyclohexylcarbodiimide (0.56 g, 2.70 mmol). The resulting solution was warmed to room temperature and stirred for 48 hours. After removal of dicyclohexylurea by filtration, the filtrate was diluted with 100 mL of ethyl acetate and washed several times with H2O. The organic was then dried (Na2SO4) and concentrated in vacuo to an oil. Chromatography (SiO2, 5% methanol/CHCl3) provided 0.84 g (34%) of (R)-1-[1-oxo-2-[4-(2-sulfobenzoyl)amino-1H-imidazol-1-yl]octyl]-4-(cis)-methanesulfonamido))-phenoxy]-L-proline methyl ester as a white solid. M.Pt. 150° C. (dec).

Workup

  1. temperatureThe resulting solution was warmed to room temperature
  2. customAfter removal of dicyclohexylurea
  3. filtrationby filtration
  4. additionthe filtrate was diluted with 100 mL of ethyl acetate
  5. washwashed several times with H2O
  6. dry with materialThe organic was then dried (Na2SO4)
  7. concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record
ord-ecf894ee13164614b42b2308d3d9f8e4
Source dataset
uspto-grants-1994_09
Patent number
US05344937

Reaction notes

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