Dicyclohexylcarbodiimide → HCID 13021285, compound

HRID 614654Notes

Reaction equation

HRID 614654 reaction equation
[C:1]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:23]([O:27][C:28](=[O:34])[C@@H:29]1[CH2:33][CH2:32][CH2:31][NH:30]1)([CH3:26])([CH3:25])[CH3:24].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.C(OCC)C>[C:23]([O:27][C:28](=[O:34])[C@@H:29]1[CH2:33][CH2:32][CH2:31][N:30]1[C:20](=[O:22])[C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 6453108L-Proline 1,1-dimethylethyl ester

Product 1

HCID 13021285HCID 13021285, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 6344DichloromethaneSolvent2×

Procedure

157 g of N-carbobenzoxy-L-phenylalanine in 500 ml methylene chloride and 300 ml absolute diethyl ether is treated at 15°-18° C. with 85.5 g L-proline tert.-butyl ester in 100 ml diethyl ether over 5 minutes, and then with 114 g of dicyclohexylcarbodiimide in 150 ml of diethyl ether over 15 minutes, both additions being at such a rate that the reaction mixture temperature does not rise above 18° C. The resultant mixture is stirred for a further hour at room temperature, and filtered, the solid residue being washed with ether. The filtrate is washed with, in turn, 2N hydrochloric acid, water, potassium bicarbonate, and then water, each washing being extracted with diethyl ether. All the organic phases are combined, dried over sodium sulphate and concentrated to yield an oily residue. The oily residue is taken up in methylene chloride, filtered, concentrated and dried in a high vacuum to yield the heading compound as a yellow oil.

Workup

  1. customdoes not rise above 18° C
  2. filtrationfiltered
  3. washthe solid residue being washed with ether
  4. washThe filtrate is washed with, in turn, 2N hydrochloric acid, water, potassium bicarbonate
  5. extractionwater, each washing being extracted with diethyl ether
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customto yield an oily residue
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried in a high vacuum

Sources & evidence

ORD record
ord-a92801fc1c2e4a5bb65e0e1c7f741894
Source dataset
uspto-grants-1979_03
Patent number
US04145549

Reaction notes

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