Hydrochloric Acid → HCID 131711705, compound

HRID 2052275Notes

Reaction equation

HRID 2052275 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:13]([NH:15][C@H:16]([C:20]([NH:22][C@H:23]([C:28]([NH:30][C@@H:31]([C:38]([NH2:40])=[O:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:24][C:25](=[O:27])[OH:26])=[O:21])[CH2:17][CH2:18][CH3:19])=[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:48].SC(O)C>O1CCOCC1>[NH2:1][C@H:2]([C:13]([NH:15][C@H:16]([C:20]([NH:22][C@H:23]([C:28]([NH:30][C@@H:31]([C:38]([NH2:40])=[O:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:24][C:25](=[O:26])[OH:27])=[O:21])[CH2:17][CH2:18][CH3:19])=[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:48]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4713212Mercapto-ethanolHCID 131711702HCID 131711702, compound

Product 1

HCID 131711705HCID 131711705, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.50 g (2.30 mmoles) of BOC-Trp-Nva-Asp-D-Phg-NH2 are treated with 20 ml of 4 n hydrochloric acid in dioxane in the presence of 0.77 ml (11 moles) of mercaptoethanol. After 30 minutes the suspension is evaporated in vacuo, the solid residue is admixed with ether, and the suspension is filtered. 1.34 g (99.0 %) of H-Trp-Nva-Asp-D-Phg-NH2.HCl are obtained; m.p.: 216° C. (decomposition), Rf7 :0.30, [α]D :-53.3° (c: 1.0, in dimethyl formamide).

Workup

  1. customAfter 30 minutes the suspension is evaporated in vacuo
  2. filtrationthe suspension is filtered

Sources & evidence

ORD record
ord-8e397efb39c74c478defa7bc37745b44
Source dataset
uspto-grants-1980_01
Patent number
US04183909

Reaction notes

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