Chemical process
AssigneeAtraZeneca AB
InventorsNigel Phillip Taylor, Kevin William Leslie, Phillip John Hogan, Francis Joseph Montgomery, Edward John Bush, Kay Alison Boardman, Claire Ingrid Pulling, Alan Charles Barker
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Abstract
A process for the preparation of a salt of 5-phenylpentanoyl-(S)-arginyl-(S)-alanyl-{(S)-2-[(R)-3-amino-2-oxopyrrolidin-1-yl]propionyl}-(S)-alanyl-(S)-arginyl-(S)-alanyl-4-aminophenylacetamide (SEQ ID NO: 1) which comprises deprotection of a compound of the formula II or a salt thereof: wherein Pg and R1 are defined in the description. Also claimed are intermediates used in the process and the processes for the preparation of the intermediates.
Claims35
A process for the manufacture of a salt of the compound of formula I:
- 19
- which comprises deprotection of a compound of the formula II or a salt thereof:
- 20
- wherein:
- each Pg is, independently, an arginine protecting group;
- and
- R1 is hydrogen or a protecting group for an amino group of an acetamide moiety.
The compound (S)-2-[(R)-3-(N-[tert-butyloxycarbonyl]amino)-2-oxopyrrolidin-1-yl]propionic acid.
The compound of the Formula XIIa:
- 33
- wherein R1 is a protecting group for an amino group of an acetamide moiety;
- and
- Z1 is H or an amino protecting group.
A process for preparing of 4-aminophenylacetamide comprising the steps:
- (i) esterification of 4-aminophenylacetic acid with a suitable alcohol in the presence of sulphuric acid to give a 4-aminophenylacetate ester hydrogensulphate salt;
- and
- (ii) reacting the product of step (i) with ammonia.
Dependencies are inferred from the claim text.