Dichloromethane → HCID 131721057, compound

HRID 341746Notes

Reaction equation

HRID 341746 reaction equation
[CH2:1]1CCC(N=C=N[CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)C[CH2:2]1.[CH:16]1[CH:17]=[CH:18][C:19]2N(O)N=N[C:20]=2[CH:21]=1.[CH3:26][CH:27]([CH2:29][C@H:30]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:31]([OH:33])=[O:32])[CH3:28].[CH2:42](Cl)[Cl:43]>>[NH:34]([C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])[C@H:30]([C:31]([OH:33])=[O:32])[CH2:29][CH:27]([CH3:28])[CH3:26].[CH3:42][C:20]1[CH:21]=[CH:16][C:17]([CH:30]([NH2:34])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:18][CH:19]=1.[CH2:1]=[CH:2][C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:21]=1.[CH2:16]=[CH:21][C:10]1[CH:11]=[CH:12][C:13]([CH:26]=[CH2:27])=[CH:14][CH:15]=1.[ClH:43]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

Product 1

HCID 131721057HCID 131721057, compound

Procedure

Separately, 2 mmol amino-group-protected amino acid Boc-Leu--OH corresponding to the amino acid residue at the 27-position in SEQ ID NO:1 was dissolved in 4 ml DCM. This solution was introduced into a vessel for amino acid activation, and after 3 ml DCC (0.5M in DCM) and 4 ml HOBt (0.5M in DCM) were added to it, and they were reacted for 30 minutes. Thereafter, the reaction solution was filtered off and the filtrate was transferred to a concentration vessel. 3 ml DMF was added to it and the DCM was distilled off in an argon stream. Then, 3 ml DMF was added to the concentrate, and it was transferred to the above reactor for peptide solid-phase synthesis and reacted for 30 minutes. Then, the reaction mixture was washed with 8 ml DCM (6 times, 20 seconds each). Separately, 2 mmol Boc-Leu--OH was dissolved in 4 ml DCM and the solution was introduced into the reactor for amino acid activation and the same procedure as described above was repeated (double-coupling) and filtered. Boc-Leu-MBHA resin was thus obtained.

Workup

  1. customwere reacted for 30 minutes
  2. filtrationThereafter, the reaction solution was filtered off
  3. customthe filtrate was transferred to a concentration vessel
  4. addition3 ml DMF was added to it
  5. distillationthe DCM was distilled off in an argon stream
  6. additionThen, 3 ml DMF was added to the concentrate, and it
  7. customwas transferred to the above reactor for peptide solid-phase synthesis
  8. customreacted for 30 minutes
  9. washThen, the reaction mixture was washed with 8 ml DCM (6 times, 20 seconds each)
  10. filtrationfiltered

Sources & evidence

ORD record
ord-bebe2ea2acbb48a087d3f3468f48fc0e
Source dataset
uspto-grants-1999_01
Patent number
US05856303

Reaction notes

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