Dicyclohexylcarbodiimide → N-(Benzyloxycarbonyl)-D-tryptophan

HRID 2083839Notes

Reaction equation

HRID 2083839 reaction equation
Cl.C[O:3]C(=O)[C@H](CC(C)C)N.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.COC(=O)[C@H](CC(C)C)N[C:42](=[O:65])[C@@H:43]([CH2:55][C:56]1[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[NH:58][CH:57]=1)[NH:44][C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46]>CO.C(N(CC)CC)C.CN(C)C=O>[CH2:48]([O:47][C:45]([NH:44][C@@H:43]([C:42]([OH:65])=[O:3])[CH2:55][C:56]1[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[NH:58][CH:57]=1)=[O:46])[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2723695Leucine methyl ester hydrochlorideHCID 54062429Nalpha-benzyloxycarbonyl-D-tryptophyl-L-leucine methyl ester

Product 1

HCID 700663N-(Benzyloxycarbonyl)-D-tryptophan

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

, and L-leucine methyl ester hydrochloride 3.96 g., are dissolved in 60 ml. of dimethylformamide, cooled in an ice bath and 2.77 ml., of triethylamine added dropwise. The stirred and cooled solution is then treated with 2.97 g. of 1-hydroxy-benzotriazole and 4.53 g. of dicyclohexylcarbodiimide. The reaction is stirred to room temperature in the melting ice bath and for twenty-four additional hours at room temperature. It is then filtered and the solvent evaporated under reduced pressure. The residue is dissolved in 300 ml. of ethyl acetate and the solution is washed with 0.5 N hydrochloric acid, saturated sodium chloride solution, twice with 5% sodium bicarbonate solution and finally with a saturated sodium chloride solution. The ethyl acetate solution is dried over magnesium sulfate and the solvent evaporated to leave a crystalline solid. The product is crystallized from 125 ml. of hot methanol to give 4.3 g. of Nα -benzyloxycarbonyl-D-tryptophyl-L-leucine methyl ester, mp. 155°-156° C; [α]D23 -21.8°, (c 2.03, methanol).

Workup

  1. dissolution, are dissolved in 60 ml
  2. temperaturecooled solution
  3. additionis then treated with 2.97 g
  4. filtrationIt is then filtered
  5. customthe solvent evaporated under reduced pressure
  6. dissolutionThe residue is dissolved in 300 ml
  7. washof ethyl acetate and the solution is washed with 0.5 N hydrochloric acid, saturated sodium chloride solution, twice with 5% sodium bicarbonate solution and finally with a saturated sodium chloride solution
  8. dry with materialThe ethyl acetate solution is dried over magnesium sulfate
  9. customthe solvent evaporated
  10. customto leave a crystalline solid
  11. customThe product is crystallized from 125 ml
  12. customof hot methanol to give 4.3 g

Sources & evidence

ORD record
ord-e94e2b47f30d4de693d76125fcb9caef
Source dataset
uspto-grants-1978_04
Patent number
US04086219

Reaction notes

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