Dicyclohexylcarbodiimide → HCID 131720711, compound

HRID 963950Notes

Reaction equation

HRID 963950 reaction equation
[NH2:1][C@H:2]([C:10]([NH2:12])=[O:11])[CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][CH:5]=1.Cl.Cl.[NH:15]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:16]([C:23](O)=[O:24])[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C1(N=C=NC2CCCCC2)CCCCC1.OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[NH:15]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:16]([C:23]([NH:1][C@H:2]([C:10]([NH2:12])=[O:11])[CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][CH:5]=1)=[O:24])[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

8

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 7004938N-(tert-Butoxycarbonyl)-L-cyclohexylglycineHCID 131720712HCID 131720712, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 131720711HCID 131720711, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Stir overnight H-(L)-Pal-NH2.2HCl (432 mg, 1.82 mmol), Boc-(L)-Chg-OH (609 mg, 2.37 mmol, 1.3 equivalent), dicyclohexylcarbodiimide (494 mg, 2.4 mmol), hydroxybenzotriazole (324 mg, 2.4 mmol) and diisopropylethylamine (4 mmol) in dimethyl formamide (15 mL). Evaporate dimethyl formamide, add ethyl acetate and store the mixture at room temperature for 1 h. Filter off the diisopropylcarbodiimidecyclohexylurea formed, extract the solution by a saturated solution of sodium bicarbonate (3×), dry over magnesium sulfate, and evaporate. Crystallize by addition of hexanes to give Boc-(L)-Chg-(L)-Pal-NH2 (598 mg, 81%).

Workup

  1. filtrationFilter off the diisopropylcarbodiimidecyclohexylurea
  2. customformed
  3. extractionextract the solution by a saturated solution of sodium bicarbonate (3×)
  4. dry with materialdry over magnesium sulfate
  5. customevaporate
  6. customCrystallize by addition of hexanes

Sources & evidence

ORD record
ord-8485fb6095294a44902f31c3f2391e36
Source dataset
uspto-grants-1998_06
Patent number
US05766932

Reaction notes

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