Diethyl Ether → HCID 131714286, compound

HRID 371358Notes

Reaction equation

HRID 371358 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:4]([NH:6][C@H:7]([C:16]([NH:18][CH2:19][C:20]([NH:22][C@H:23]([C:34]([NH:36][C@H:37]([C:42]([NH:44][C@H:45]([C:50]([NH:52][C@H:53]([C:61]([NH2:63])=[O:62])[CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:51])[CH2:46][C:47](=[O:49])[OH:48])=[O:43])[CH2:38][CH2:39][S:40][CH3:41])=[O:35])[CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)=[O:21])=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)=[O:5])[CH3:3].CCOCC>FC(F)(F)C(O)=O.C(S)(S)C>[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:16]([NH:18][CH2:19][C:20]([NH:22][C@H:23]([C:34]([NH:36][C@H:37]([C:42]([NH:44][C@H:45]([C:50]([NH:52][C@H:53]([C:61]([NH2:63])=[O:62])[CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)=[O:51])[CH2:46][C:47](=[O:48])[OH:49])=[O:43])[CH2:38][CH2:39][S:40][CH3:41])=[O:35])[CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)=[O:21])=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)=[O:5])[CH3:3]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 13503189HCID 13503189, compound

Product 1

HCID 131714286HCID 131714286, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 336451,1-EthanedithiolSolvent

Conditions

Temperature
4 °C

Procedure

1.00 g of Boc-Ala-Tyr-Gly-Trp-Met-Asp-Phe-NH2 (m.p. 197°-200° C. Anal. Calcd. (%) for C48H61N9O12S: C, 58.35; H, 6.22; N, 12.75. Found (%): C, 58.35; H, 6.43; N, 12.61) was dissolved in 5 ml of trifluoroacetic acid containing 0.2 ml of ethanedithiol and reacted at room temperature for 30 minutes. Then 100 ml of anhydrous ether was added to the reaction mixture, and the resulting precipitate was filtered and dried. This deprotected heptapeptide was dissolved in 20 ml of DMF containing 0.14 ml of triethylamine, and 0.40 g of glutaric anhydride was added under cooling with ice. After 17-hour stirring at 4° C., the reaction mixture was distilled in vacuo to remove the solvent, and 1N citric acid was added to the residue to form a precipitate. It was washed with water and recrystallized from 20 ml of methanol, giving 0.77 g of Glt-Ala-Tyr-Gly-Trp-Met-Asp-Phe-NH2 ; yield 76.1%, m.p. 167°-170° C.

Workup

  1. customreacted at room temperature for 30 minutes
  2. filtrationthe resulting precipitate was filtered
  3. customdried
  4. dissolutionThis deprotected heptapeptide was dissolved in 20 ml of DMF containing 0.14 ml of triethylamine, and 0.40 g of glutaric anhydride
  5. additionwas added
  6. temperatureunder cooling with ice
  7. distillationthe reaction mixture was distilled in vacuo
  8. customto remove the solvent, and 1N citric acid
  9. additionwas added to the residue
  10. customto form a precipitate
  11. washIt was washed with water
  12. customrecrystallized from 20 ml of methanol

Sources & evidence

ORD record
ord-ea4f79312bb64f20a2a7aaefa0fdc628
Source dataset
uspto-grants-1985_07
Patent number
US04530836

Reaction notes

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