Hydrochloric Acid → HCID 131711700, compound

HRID 2052273Notes

Reaction equation

HRID 2052273 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:29]([NH:31][C@@H:32]([C:39]([NH2:41])=[O:40])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[CH2:25][C:26](=[O:28])[OH:27])=[O:22])[CH2:17][CH2:18][CH2:19][CH3:20])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[ClH:49].SC(O)C>O1CCOCC1>[NH2:1][C@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:29]([NH:31][C@@H:32]([C:39]([NH2:41])=[O:40])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[CH2:25][C:26](=[O:27])[OH:28])=[O:22])[CH2:17][CH2:18][CH2:19][CH3:20])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[ClH:49]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4713212Mercapto-ethanolHCID 131711697HCID 131711697, compound

Product 1

HCID 131711700HCID 131711700, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.20 g (3.32 mmoles) of BOC-Trp-Nle-Asp-D-Phg-NH2 are treated with 25 ml of 4 n hydrochloric acid in dioxane in the presence of 1.20 ml (17 mmoles) of mercaptoethanol. After 15 minutes the solution is evaporated in vacuo, the residue is triturated with ether, and the solid is filtered off. 1.99 g (99.0%) of H-Trp-Nle-Asp-D-Phg-NH2.HCl are obtained; m.p.: 217°-221° C. (decomposition), Rf7 :0.35, [α]D :-54.2° (c: 1.0, in dimethyl formamide).

Workup

  1. customAfter 15 minutes the solution is evaporated in vacuo
  2. customthe residue is triturated with ether
  3. filtrationthe solid is filtered off

Sources & evidence

ORD record
ord-ee3ef9bcea594fca964243d3187c2396
Source dataset
uspto-grants-1980_01
Patent number
US04183909

Reaction notes

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