Hydrochloric Acid → HCID 131711689, compound

HRID 2052267Notes

Reaction equation

HRID 2052267 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][S: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.O1CCOCC1.Cl.SC(O)C>CCOCC>[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][S: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

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 4713212Mercapto-ethanolHCID 131711690HCID 131711690, compound

Product 1

HCID 131711689HCID 131711689, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6.0 g (88.8 mmoles) of BOC-Trp-Met-Asp-D-Phg-NH2, prepared as described in Example 1, Step 7, are treated with 60 ml of a dioxane solution of hydrochloric acid in the presence of 3.1 ml (44 mmoles) of mercaptoethanol. After 15 minutes the reaction mixture is diluted with dry ether, and the separated solids are filtered off. The resulting 6.23 g. of hydrochloride, containing a large excess of hydrochloric acid, is suspended in 150 ml of water, the suspension is neutralized (pH=7) with triethylamine, stirred, and the precipitate is filtered off and washed with water. 4.0 g (78%) of H-Trp-Met-Asp-D-Phg-NH2 are obtained; m.p.: 230°-232° C. (decomposition); Rf7 =0.3.

Workup

  1. filtrationthe separated solids are filtered off
  2. additionof hydrochloride, containing a large excess of hydrochloric acid
  3. filtrationthe precipitate is filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-e94411816f8d4ae4b0d4063fc9d4556d
Source dataset
uspto-grants-1980_01
Patent number
US04183909

Reaction notes

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