Dicyclohexylcarbodiimide → Z-Ser-NHNH-Boc

HRID 2119110Notes

Reaction equation

HRID 2119110 reaction equation
[NH:1]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C@H:2]([C:5]([OH:7])=O)[CH2:3][OH:4].[C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])[NH:19][NH2:20].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:1]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C@H:2]([C:5]([NH:20][NH:19][C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:7])[CH2:3][OH:4]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 70091tert-Butyl carbazateHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 100310N-(Benzyloxycarbonyl)-L-serine

Product 1

HCID 13469056Z-Ser-NHNH-Boc

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Z-Ser-OH (10.0 g) and 6.2 g of t-butyl carbazate were dissolved in 150 ml of DMF and the solution was ice-cooled. HONB (8.0 g) and 9.3 g of DCC were added and the mixture was stirred for 15 hours. The formed DCU was filtered off and the filtrate was concentrated. The residue was extracted into AcOEt and the AcOEt solution was washed with 4% aqueous NaHCO3 and 10% aqueous citric acid, dried over Na2SO4 and concentrated. Ether was added and the crystals was collected by filtration. Yield 7.3 g (50.4%), mp 95°-98° C., [α]D26 -6.2° (c=0.8, DMF), Rf1 0.62.

Workup

  1. temperaturecooled
  2. filtrationThe formed DCU was filtered off
  3. concentrationthe filtrate was concentrated
  4. extractionThe residue was extracted into AcOEt
  5. washthe AcOEt solution was washed with 4% aqueous NaHCO3 and 10% aqueous citric acid
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. additionEther was added
  9. filtrationthe crystals was collected by filtration

Sources & evidence

ORD record
ord-80daa5f88ed14b4a94aff7fb10fdef83
Source dataset
uspto-grants-1987_07
Patent number
US04681848

Reaction notes

Loading…