Dicyclohexylcarbodiimide → HCID 86749823, compound

HRID 743672Notes

Reaction equation

HRID 743672 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([NH:13][C@H:14]([C:42]([OH:44])=O)[CH2:15][C:16](=[O:41])[NH:17][C@@H:18]2[O:35][C@H:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[C@@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:19]2[O:20][C:21](=[O:23])[CH3:22])(=[O:12])=[O:11])=[C:5]([CH3:45])[C:4]=1[CH3:46].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[ClH:72].[C:73]([C:76]1[CH:92]=[CH:91][C:79]([CH2:80][C@H:81]([C:83]([N:85]2[CH2:90][CH2:89][CH2:88][CH2:87][CH2:86]2)=[O:84])[NH2:82])=[CH:78][CH:77]=1)(=[NH:75])[NH2:74]>CN(C=O)C>[ClH:72].[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([NH:13][C@H:14]([C:42]([NH:82][C@@H:81]([C:83]([N:85]2[CH2:90][CH2:89][CH2:88][CH2:87][CH2:86]2)=[O:84])[CH2:80][C:79]2[CH:91]=[CH:92][C:76]([C:73](=[NH:74])[NH2:75])=[CH:77][CH:78]=2)=[O:44])[CH2:15][C:16](=[O:41])[NH:17][C@@H:18]2[O:35][C@H:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[C@@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:19]2[O:20][C:21](=[O:23])[CH3:22])(=[O:12])=[O:11])=[C:5]([CH3:45])[C:4]=1[CH3:46]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 22865519HCID 22865519, compoundHCID 22865525HCID 22865525, compound

Product 1

HCID 86749823HCID 86749823, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 20 (2.50 g), HOBt (0.65 g) and DCCI (1.15 g) were dissolved in DMF (100 mL) and after 1 h 4-amidino-D-phenylalanine-piperidide hydrochloride (1.50 g) was mixed in. The mixture was stirred for a further 24 h and concentrated by evaporation in vacuo. The residue was dissolved in chloroform and washed with water. The organic phase was concentrated in vacuo. The crude product obtained was purified by column chromatography on silica gel with chloroform and methanol 3:1.

Workup

  1. additionwas mixed in
  2. concentrationconcentrated by evaporation in vacuo
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with water
  5. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-eef6a0438ef84ab5947536f0ebb04d64
Source dataset
uspto-grants-1996_09
Patent number
US05556941

Reaction notes

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