Acetic Acid → methyl L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate hydrochloride

HRID 1680568Notes

Reaction equation

HRID 1680568 reaction equation
C(O)(=O)C.[ClH:5].C([NH:13][C@H:14]([C:23]([NH:25][C@@H:26]([C:31]([NH:33][CH2:34][C:35]([NH:37][C@H:38]([C:46]([CH:48]1[C:55]2([NH2:57])[CH2:56][CH:51]3[CH2:52][CH:53]([CH2:58][C:49]1([C:59]([O:61][CH3:62])=[O:60])[CH2:50]3)[CH2:54]2)=[O:47])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:36])=[O:32])[CH2:27][CH2:28][S:29][CH3:30])=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(OC(C)(C)C)=O>O1CCOCC1>[ClH:5].[NH2:13][C@H:14]([C:23]([NH:25][C@@H:26]([C:31]([NH:33][CH2:34][C:35]([NH:37][C@H:38]([C:46]([CH:48]1[C:55]2([NH2:57])[CH2:56][CH:51]3[CH2:52][CH:53]([CH2:58][C:49]1([C:59]([O:61][CH3:62])=[O:60])[CH2:50]3)[CH2:54]2)=[O:47])[CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:36])=[O:32])[CH2:27][CH2:28][S:29][CH3:30])=[O:24])[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 70566106methyl Boc-L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate

Product 1

HCID 70565529methyl L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a mixture of 5.0 ml acetic acid, 5.0 ml dioxane and 10.0 ml of a 6 M solution of hydrogen chloride in dioxane is added 1.0 g of methyl Boc-L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate. The reaction mixture is allowed to stand for 30 minutes at room temperature then the solvent is removed by vacuum distillation. The residue is dissolved in a mixture of 2.0 ml methanol and 20 ml water and the solution is lyophilized to give methyl L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate hydrochloride which is represented by the following formula ##STR20##

Workup

  1. customthe solvent is removed by vacuum distillation
  2. dissolutionThe residue is dissolved in a mixture of 2.0 ml methanol and 20 ml water

Sources & evidence

ORD record
ord-f1a39a7f8e11445e973f030e7b69d98b
Source dataset
uspto-grants-1981_06
Patent number
US04273704

Reaction notes

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