Dicyclohexylcarbodiimide → HCID 131712284, compound

HRID 1277397Notes

Reaction equation

HRID 1277397 reaction equation
[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@@H:2]([C:6]([OH:8])=O)[C@H:3]([CH3:5])[OH:4].[NH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@@H:2]([C:6]([NH:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:8])[C@H:3]([CH3:5])[OH:4]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 151417Glycine tert-butyl esterHCID 853484Z-D-Thr-OH

Product 1

HCID 131712284HCID 131712284, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of THF are dissolved 5.0 g of Z-(D)-Thr-OH and 3.6 g of H-Gly-OBut. After cooling, 3.9 g of HONB and 4.5 g of DCC are added, and the mixture is stirred overnight. The solvent is distilled off, and the residue is extracted with 100 ml of AcOEt, followed by washing with water and drying over anhydrous sodium sulphate. The AcOEt is distilled off, and the residue is treated with petroleum ether. Recrystallization from AcOEt-petroleum ether yields 5.0 g of the desired compound. m.p. 56°-57° C., [α]D23 +13.8° (c=0.5, MeOH), Rf1 =0.69.

Workup

  1. temperatureAfter cooling
  2. distillationThe solvent is distilled off
  3. extractionthe residue is extracted with 100 ml of AcOEt
  4. washby washing with water
  5. dry with materialdrying over anhydrous sodium sulphate
  6. distillationThe AcOEt is distilled off
  7. additionthe residue is treated with petroleum ether
  8. customRecrystallization from AcOEt-petroleum ether

Sources & evidence

ORD record
ord-fa8911d41a0d4cfe9c9b18dd77cd9ea5
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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