p-Toluenesulfonate → 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

HRID 1455166

Reaction equation

HRID 1455166 reaction equation
C([C@@H](N[C@H](C(O)=O)C)CCC1C=CC=CC=1)(OCC)=O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH2:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35][C@@H:34]([C:42]([OH:44])=[O:43])[NH:33]1>>[CH2:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35][CH:34]([C:42]([OH:44])=[O:43])[NH:33]1

Participants

4

Reactant 3

HCID 85570p-ToluenesulfonateHCID 2733226(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acidHCID 5702571N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanine

Product 1

HCID 954891,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

Procedure

The first step of Method-I consists of condensation of N-[1(S)-carboethoxy-3-phenylpropyl]-(S)-alanine (III) with the para-toluene sulfonate salt of the benzyl ester of (S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid (IV) to give the benzyl ester of (S, S, S)-2-{2-{(1-ethoxycarbonyl)-3-phenylpropyl)amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid or quinapril benzyl ester which is isolated as the maleic acid salt (V).

Sources & evidence

ORD record
ord-ab98451813ec47e8a626bbdb71ae2dfa
Source dataset
uspto-grants-2009_01
Patent number
US07482361B2

Linked notes

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