HCID 10722406, compound → HCID 10767930, compound

HRID 1440169Notes

Reaction equation

HRID 1440169 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:21]([NH:23][C@@H:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:26][CH2:27][CH3:28])=[O:22])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:5]=1[Cl:20]>C(O)=O>[NH2:1][C@@H:2]([C:21]([NH:23][C@@H:24]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:25][CH2:26][CH2:27][CH3:28])=[O:22])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])[C:5]=1[Cl:20]

Participants

3

Reactant 1

HCID 10722406HCID 10722406, compound

Product 1

HCID 10767930HCID 10767930, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of Boc-DTrp(1-Boc,2-Cl)-DNle-OtBu (252 mg, prepared in (3)) in formic acid (10 ml) was stirred at room temperature for 1 h. The mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (50 ml). The solution was washed with sat. aq. NaHCO3 (50 ml×2) and sat. brine (50 ml) successively, dried over MgSO4 and evaporated in vacuo. The residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=30/1 for development to give the product (98 mg).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  3. washThe solution was washed with sat. aq. NaHCO3 (50 ml×2) and sat. brine (50 ml) successively
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=30/1 for development

Sources & evidence

ORD record
ord-7078a04e3cd34a5fa23c45f853b8021a
Source dataset
uspto-grants-1996_03
Patent number
US05496928

Reaction notes

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