Hydrochloric Acid → HCID 131717767, compound

HRID 2082225Notes

Reaction equation

HRID 2082225 reaction equation
[NH:1]([C:56]([O:58]C(C)(C)C)=O)[C@H:2]([C:18]([NH:20][C@@H:21]([C:34]([NH:36][C@H:37]([C:45]([N:47]([CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH3:48])=[O:46])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:35])[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]([CH:32]=[O:33])[CH:24]=1)=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].Cl.[CH2:64](Cl)Cl>>[NH:1]([C:56]([CH3:64])=[O:58])[C@H:2]([C:18]([NH:20][C@@H:21]([C:34]([NH:36][C@H:37]([C:45]([N:47]([CH2:49][C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)[CH3:48])=[O:46])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:35])[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]([CH:32]=[O:33])[CH:24]=1)=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14999565HCID 14999565, compound

Product 1

HCID 131717767HCID 131717767, compound

Procedure

To a solution of Boc-Lys(Z)-D-Trp(CHO)-Phe-NMeBzl (1.04 g) in methylene chloride (10 ml) was added 4N-HCl/DOX (10 ml) under ice-cooling. The mixture was stirred for an hour at room temperature. After evaporation, the residue was pulverized with diisopropyl ether, filtered, washed with diisopropyl ether and dried. The obtained HCl.H-Lys(Z)-D-Trp(CHO)-Phe-NMeBzl (0.94 g) was dissolved in methylene chloride (15 ml) and cooled in an ice-bath. To the solution were added triethylamine (0.34 ml) and Ac2O (0.11 ml) and the mixture was stirred for an hour at the same temperature. After evaporation and extraction with ethyl acetate, the organic layer was washed successively with water, 2% hydrochloric acid, water, 2% sodium hydrogencarbonate, water and saturated sodium chloride, and then dried over magnesium sulfate. The evaporated residue was subjected to column chromatography on silica gel (50 g) and eluted with a mixture of chloroform and methanol (50 ml). The fractions containing the object compound were combined and evaporated. The residue was pulverized with n-hexane, filtered, washed with n-hexane and dried to give Ac-Lys(Z)-D-Trp(CHO)-Phe-NMeBzl (0.82 g).

Workup

  1. temperaturecooling
  2. customAfter evaporation
  3. filtrationfiltered
  4. washwashed with diisopropyl ether
  5. customdried
  6. dissolutionH-Lys(Z)-D-Trp(CHO)-Phe-NMeBzl (0.94 g) was dissolved in methylene chloride (15 ml)
  7. temperaturecooled in an ice-bath
  8. additionTo the solution were added triethylamine (0.34 ml) and Ac2O (0.11 ml)
  9. stirringthe mixture was stirred for an hour at the same temperature
  10. customAfter evaporation and extraction with ethyl acetate
  11. washthe organic layer was washed successively with water, 2% hydrochloric acid, water, 2% sodium hydrogencarbonate, water and saturated sodium chloride
  12. dry with materialdried over magnesium sulfate
  13. washeluted with a mixture of chloroform and methanol (50 ml)
  14. additionThe fractions containing the object compound
  15. customevaporated
  16. filtrationfiltered
  17. washwashed with n-hexane
  18. customdried

Sources & evidence

ORD record
ord-dad5302a8a8f435289ebec44ea87ac7d
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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