Water → L-methionyl-L-aspartyl-D-alanine amide hydrochloride

HRID 596804Notes

Reaction equation

HRID 596804 reaction equation
C(OC([NH:8][C@H:9]([C:14]([NH:16][C@H:17]([C:22]([NH:24][C@@H:25]([C:27]([NH2:29])=[O:28])[CH3:26])=[O:23])[CH2:18][C:19](=[O:21])[OH:20])=[O:15])[CH2:10][CH2:11][S:12][CH3:13])=O)(C)(C)C.O.[ClH:31].O1CCOCC1>C(O)(=O)C>[ClH:31].[NH2:8][C@H:9]([C:14]([NH:16][C@H:17]([C:22]([NH:24][C@@H:25]([C:27]([NH2:29])=[O:28])[CH3:26])=[O:23])[CH2:18][C:19](=[O:20])[OH:21])=[O:15])[CH2:10][CH2:11][S:12][CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 204431481,4-Dioxane hydrochlorideHCID 22796339N-t-butoxycarbonyl-L-methionyl-L-aspartyl-D-alanine amide

Product 1

HCID 22796354L-methionyl-L-aspartyl-D-alanine amide hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

12.54 Parts of N-t-butoxycarbonyl-L-methionyl-L-aspartyl-D-alanine amide is dissolved in 107 parts by volume glacial acetic acid and 51.66 parts by volume of a 5.6 M solution of HCl/dioxane. The resultant mixture is stirred for 20 minutes and then stripped under reduced pressure to afford a solid. The solid is triturated with ethyl ether, cooled, and the resultant product washed with cold ethyl ether and vacuum dried. This solid is purified by countercurrent distribution to afford L-methionyl-L-aspartyl-D-alanine amide hydrochloride hydrated with 2/3 mole of water per mole, and represented by the following formula.

Workup

  1. customto afford a solid
  2. customThe solid is triturated with ethyl ether
  3. temperaturecooled
  4. washthe resultant product washed with cold ethyl ether and vacuum
  5. customdried
  6. customThis solid is purified by countercurrent distribution

Sources & evidence

ORD record
ord-c6ddfcbe70fe4dab9a37bb9b849a37d2
Source dataset
uspto-grants-1977_03
Patent number
US04012367

Reaction notes

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