Hydrochloric Acid → HCID 14999585, compound

HRID 2082232Notes

Reaction equation

HRID 2082232 reaction equation
[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:2]([C:15](O)=[O:16])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH:13]=[O:14])[CH:5]=1.CN1CCOCC1.ClC(OCC(C)C)=O.Cl.[NH2:41][C@H:42]([C:50]([CH2:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C(Cl)Cl>[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:2]([C:15]([NH:41][C@H:42]([C:50]([CH2:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:16])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH:13]=[O:14])[CH:5]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 7021874Boc-D-Trp(For)-OHHCID 131717776HCID 131717776, compound

Product 1

HCID 14999585HCID 14999585, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Boc-D-Trp(CHO)-OH (0.92 g) in methylene chloride (15 ml) were added NMM (0.28 ml) and isobutyl chloroformate (0.36 ml) successively at -15° C., and the mixture was stirred for ten minutes. On the other hand, a solution of HCl.H-Phe-(CH2)2Ph (0.80 g) in methylene chloride (15 ml) was cooled at -30° C. and thereto was added NMM (0.28 ml). This solution was added to the above mentioned mixture at -50° C., and stirred for an hour at -50° C. and then stirred for 2 hours at room temperature. After evaporation and extraction with ethyl acetate, the organic layer was washed successively with 2% hydrochloric acid, water, 2% sodium hydrogen carbonate solution, water, and saturated sodium chloride solution, and dried over magnesium sulfate. After evaporation, the residual white crystals were filtered and washed with n-hexane. The crystals were recrystallized from ethanol to give Boc-D-Trp(CHO)-Phe-(CH2)2Ph (1.16 g).

Workup

  1. additionThis solution was added to the
  2. customat -50° C.
  3. stirringstirred for an hour at -50° C.
  4. stirringstirred for 2 hours at room temperature
  5. customAfter evaporation and extraction with ethyl acetate
  6. washthe organic layer was washed successively with 2% hydrochloric acid, water, 2% sodium hydrogen carbonate solution, water, and saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customAfter evaporation
  9. filtrationthe residual white crystals were filtered
  10. washwashed with n-hexane
  11. customThe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-cc792477039c45ee8516c3f5e5e03382
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

Loading…