Dicyclohexylcarbodiimide → HCID 131717720, compound

HRID 1646913Notes

Reaction equation

HRID 1646913 reaction equation
[NH2:1][C@@H:2]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[NH:28]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C@H:29]([C:41](O)=[O:42])[CH2:30][C:31](=[O:40])[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[NH:28]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C@H:29]([C:41]([NH:1][C@@H:2]([C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:9]=1)=[O:42])[CH2:30][C:31](=[O:40])[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1581888N-tert-Butoxycarbonyl-L-aspartic acid beta-benzyl esterHCID 40560099HCID 40560099, compound

Product 1

HCID 131717720HCID 131717720, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
4 °C

Procedure

14 g of H-D-Tyr(Bzl)-OBzl (38.7 mmoles) and 12.53 g of Boc-Asp(OBzl)-OH (38.7 mmoles) are dissolved in 145 ml of CH2Cl2. In the ice-cooled solution 8.78 g of DCC (42.5 mmoles) dissolved in 35 ml of CH2Cl2 are dropped. The mixture is left under stirring for 1 h at room temperature and for one night at 4° C. The resulting precipitate (dicyclohexylurea) is filtered off and the filtrate is evaporated to dryness under vacuum. The semi-solid residue is taken up with 170 ml of 70/30 ethanol/H2O, the mixture is refluxed while two immiscible phases are formed, and left to cool under vigorous stirring. The resulting white solid is filtered and treated again with 70/30 ethanol/H2O to reflux. Thus 20 g of Boc-Asp(OBzl)-D-Tyr(Bzl)-OBzl are obtained.

Workup

  1. additionare dropped
  2. waitThe mixture is left
  3. filtrationThe resulting precipitate (dicyclohexylurea) is filtered off
  4. customthe filtrate is evaporated to dryness under vacuum
  5. temperaturethe mixture is refluxed while two immiscible phases
  6. customare formed
  7. waitleft
  8. temperatureto cool under vigorous stirring
  9. filtrationThe resulting white solid is filtered
  10. additiontreated again with 70/30 ethanol/H2O
  11. temperatureto reflux

Sources & evidence

ORD record
ord-b890617dd3064ca997cd999ccae62420
Source dataset
uspto-grants-1993_01
Patent number
US05182265

Reaction notes

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