Dicyclohexylcarbodiimide → HCID 131710222, compound

HRID 1076428Notes

Reaction equation

HRID 1076428 reaction equation
[NH2:1][C@H:2]([C:12]([NH:14][C@H:15]([C:19]([NH:21][C@H:22]([C:27]([OH:29])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:3][S:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH:30]([C:79]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:80])[C@H:31]([C:41]([NH:43][C@H:44]([C:47]([NH:49][C@H:50]([C:55]([NH:57][C@H:58]([C:63]([NH:65][C@H:66]([C:69]([NH:71][C@H:72]([C:76](O)=[O:77])[C@@H:73]([CH3:75])[OH:74])=[O:70])[CH2:67][OH:68])=[O:64])[CH2:59][CH:60]([CH3:62])[CH3:61])=[O:56])[CH2:51][C:52](=[O:54])[NH2:53])=[O:48])[CH2:45][OH:46])=[O:42])[CH2:32][S:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.C(N(CC)CC)C>[NH:30]([C:79]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:80])[C@H:31]([C:41]([NH:43][C@H:44]([C:47]([NH:49][C@H:50]([C:55]([NH:57][C@H:58]([C:63]([NH:65][C@H:66]([C:69]([NH:71][C@H:72]([C:76]([NH:1][C@H:2]([C:12]([NH:14][C@H:15]([C:19]([NH:21][C@H:22]([C:27]([OH:29])=[O:28])[CH2:23][CH:24]([CH3:25])[CH3:26])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:3][S:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:77])[C@@H:73]([CH3:75])[OH:74])=[O:70])[CH2:67][OH:68])=[O:64])[CH2:59][CH:60]([CH3:62])[CH3:61])=[O:56])[CH2:51][C:52](=[O:54])[NH2:53])=[O:48])[CH2:45][OH:46])=[O:42])[CH2:32][S:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 131710220HCID 131710220, compoundHCID 131710223HCID 131710223, compound

Product 1

HCID 131710222HCID 131710222, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8471TriethylamineSolvent

Procedure

3.90 g (6 mmols) of H-Cys(Bzl)-Val-Leu-OH, 1.15TFA are dissolved in freshly distilled dimethylformamide, treated with 4.48 g (5.5 mmols) of BOC-Cys(Bzl)-Ser-Asn-Leu-Ser-Thr-OH and stirred at room temperature until all is dissolved. The solution is then cooled to 0°C, 1.26 g (11 mmols) of N-hydroxysuccinimide and 0.98 ml of triethylamine in 45 ml of dimethylformamide are added, followed by cooling to -22°C and the addition of 1.13 g (5.5 mmols) of dicyclohexylcarbodimide in 10 ml of dimethylformamide. The batch is stirred for 1 hour at -22°C, then at room temperature for 3 days, filtered to remove precipitated dicyclohexylurea, and evaporated to dryness. The residue is stirred twice with a mixture of 200 ml of ethyl acetate and 20 ml of 5% citric acid solution, then once with a mixture of 200 ml of ethyl acetate and 20 ml of 5% sodium bicabonate solution. The resulting product is filtered off and dried at 40°C in a high vacuum. Melting point: 218°-221°C; [α]D20 -28.5° (c = 2 in dimethylformamide); Rf8 = 0.43.

Workup

  1. dissolutionall is dissolved
  2. temperatureThe solution is then cooled to 0°C
  3. temperatureby cooling to -22°C
  4. stirringThe batch is stirred for 1 hour at -22°C
  5. filtrationfiltered
  6. customto remove
  7. customprecipitated dicyclohexylurea
  8. customevaporated to dryness
  9. stirringThe residue is stirred twice with a mixture of 200 ml of ethyl acetate and 20 ml of 5% citric acid solution
  10. additiononce with a mixture of 200 ml of ethyl acetate and 20 ml of 5% sodium bicabonate solution
  11. filtrationThe resulting product is filtered off
  12. customdried at 40°C in a high vacuum

Sources & evidence

ORD record
ord-26a5788240424d98825fa76f58af8f6e
Source dataset
uspto-grants-1976_05
Patent number
US03956260

Reaction notes

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