Dicyclohexylcarbodiimide → HCID 131710225, compound

HRID 1076430Notes

Reaction equation

HRID 1076430 reaction equation
[NH:1]([C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][CH2:17][C:18]([N:20]1[CH2:27][CH2:26][CH2:25][C@H:21]1[C:22](O)=[O:23])=[O:19])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[NH2:38][C@H:39]([C:49]([NH:51][C@H:52]([C:60]([N:62]1[CH2:73][CH2:72][CH2:71][C@H:63]1[C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])=[O:61])[C@@H:53]([CH3:59])[O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:50])[CH2:40][CH2:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[CH:11]1[CH:10]=[CH:9][C:8]([CH2:7][C@H:6]([NH:5][C:3]([CH2:2][NH:1][C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])=[O:4])[C:14]([OH:15])=[O:43])=[CH:13][CH:12]=1.[NH2:16][CH2:17][C:18]([N:20]1[CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([NH:38][C@H:39]([C:49]([NH:51][C@H:52]([C:60]([N:62]1[CH2:73][CH2:72][CH2:71][C@H:63]1[C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])=[O:61])[C@@H:53]([CH3:59])[O:54][C:55]([CH3:56])([CH3:57])[CH3:58])=[O:50])[CH2:40][CH2:41][C:42](=[O:48])[O:43][C:44]([CH3:46])([CH3:45])[CH3:47])=[O:23])=[O:19]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 131710217HCID 131710217, compoundHCID 131710227HCID 131710227, compound

Product 1

HCID 131710225HCID 131710225, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

667 mg of Z-Gly-Phe-Gly-Pro-OH are dissolved in 20 ml of acetonitrile together with 608 mg of H-Glu(OtBu)-Thr(tBu)-Pro-OtBu obtained under 4 and after the addition of 222 mg of N-hydroxysuccinimide and 269 mg of dicyclohexylcarbodiimide, stirred for 16 hours at room temperature. The precipitated dicyclohexyl urea is filtered off, the filtrate . evaporated, the residue dissolved in much ethyl acetate and the solution washed as described under 1, above. After drying and evaporation of the solution in vacuo, the crude product is purified by chromatography on a column of silica gel. It can be eluted with ethyl acetate an ethyl acetate×ethanol (4:1). It is then reprecipitated from ether. Melting point: 96° - 99°C. Thin-layer chromatogram on silica gel: RfCHCl3-MeOH(δ:1) = 0.40; Rf102A = 0.75; Rf52 = 0.80

Workup

  1. customobtained under 4
  2. filtrationThe precipitated dicyclohexyl urea is filtered off
  3. customevaporated
  4. dissolutionthe residue dissolved in much ethyl acetate
  5. washthe solution washed
  6. customAfter drying
  7. customevaporation of the solution in vacuo
  8. customthe crude product is purified by chromatography on a column of silica gel
  9. washIt can be eluted with ethyl acetate an ethyl acetate×ethanol (4:1)
  10. customIt is then reprecipitated from ether

Sources & evidence

ORD record
ord-1a875ac9df53477490f5afabf9fef8f6
Source dataset
uspto-grants-1976_05
Patent number
US03956260

Reaction notes

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