Diisopropyl Ether → HCID 178455965, compound

HRID 1982308Notes

Reaction equation

HRID 1982308 reaction equation
[NH:1]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C@H:2]([C:7]([O:9]N1C(=O)CCC1=O)=O)[C@H:3]([CH2:5][CH3:6])[CH3:4].CCN(CC)CC.C(OC(C)C)(C)C.[NH2:41][C@H:42]([C:49]([NH:51][C@H:52]([C:65]([O:67][CH3:68])=[O:66])[CH2:53][CH2:54][CH2:55][CH2:56][NH:57][C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])=[O:50])[CH2:43][C:44]1[N:48]=[CH:47][NH:46][CH:45]=1>CN(C=O)C>[NH:1]([C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])[C@H:2]([C:7]([NH:41][C@H:42]([C:49]([NH:51][C@H:52]([C:65]([O:67][CH3:68])=[O:66])[CH2:53][CH2:54][CH2:55][CH2:56][NH:57][C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])=[O:50])[CH2:43][C:44]1[N:48]=[CH:47][NH:46][CH:45]=1)=[O:9])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 13361528Z-Ile-OSuHCID 178501448H-His-Lys(Boc)-OMe

Product 1

HCID 178455965HCID 178455965, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.32 g of Z-Ile-OSu [G. W. Anderson et. al., J. Amer. Chem. Soc. 86, 1839 (1964)] are dissolved in the above solution of H-His-Lys(Boc)-OMe in approximately 10 ml of DMF and mixed with 0.41 ml of NEt3. The whole is left to stand for 8 hours at room temperature, 15 ml of diisopropyl ether are added, and the whole is homogenised and filtered. The residue obtained by filtering with suction is dissolved in 15 ml of methanol and added at 0° to 23 ml of aqueous NaHCO3 solution. The resulting precipitate is filtered off, washed with H2O, dried and dissolved and reprecipitated from MeOH/ethyl acetate/petroleum ether, yielding Z-Ile-His-Lys(Boc)-OMe in the form of amorphous powder; Rf (B)=0.65; Rf (I)=0.48.

Workup

  1. waitThe whole is left
  2. filtrationfiltered
  3. customThe residue obtained
  4. filtrationby filtering with suction
  5. dissolutionis dissolved in 15 ml of methanol
  6. additionadded at 0° to 23 ml of aqueous NaHCO3 solution
  7. filtrationThe resulting precipitate is filtered off
  8. washwashed with H2O
  9. customdried
  10. dissolutiondissolved
  11. customreprecipitated from MeOH/ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-ce8789a81b9d458eb11bf86f4f86ebac
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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