Dicyclohexylcarbodiimide → HCID 13384501, compound

HRID 1253098Notes

Reaction equation

HRID 1253098 reaction equation
[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C@H:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[OH:13])[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:5])[CH3:3].[NH:19]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:20]([C@H:25]([CH2:27][C:28](O)=[O:29])[OH:26])[CH2:21][CH:22]([CH3:24])[CH3:23].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[NH:19]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[C@H:20]([C@H:25]([CH2:27][C:28]([NH:1][C@H:2]([C:4]([NH:6][C@H:7]([C@H:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[OH:13])[CH2:8][CH:9]([CH3:10])[CH3:11])=[O:5])[CH3:3])=[O:29])[OH:26])[CH2:21][CH:22]([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 2755962(3S,4S)-4-((tert-Butoxycarbonyl)amino)-3-hydroxy-6-methylheptanoic acidHCID 13384499HCID 13384499, compound

Product 1

HCID 13384501HCID 13384501, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

960 mg of H-Ala-Sta-OMe, 1 g of Boc-Sta-OH, 420 mg of HONSu and 750 mg of DCCI are dissolved successively in 50 ml of CH2Cl2 at RT. A white precipitate appears very quickly. The mixture is stirred at RT and, after 7 h, the DCU formed is filtered off and washed with CH2Cl2. The organic solution is washed successively with KHSO4 --K2SO4 (5% solution in H2O) and NaHCO3 (5% solution in H2O). It is dried over MgSO4 and filtered and the solvent is evaporated off. The product is solubilized in the minimum quantity of a chloroform/MeOH mixture (97.5/2.5, vol/vol) and deposited on the top of a column of silica gel; elution is carried out with the same mixture and the eluate is fractionated.

Workup

  1. customthe DCU formed
  2. filtrationis filtered off
  3. washwashed with CH2Cl2
  4. washThe organic solution is washed successively with KHSO4
  5. dry with materialIt is dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent is evaporated off
  8. washelution

Sources & evidence

ORD record
ord-a1e40d06942d4e78bc5d734c34b166d9
Source dataset
uspto-grants-1988_05
Patent number
US04746648

Reaction notes

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