Triethylamine → Dicyclohexylcarbodiimide

HRID 273474

Reaction equation

CCC[C@H](N[C@H](C([N:15]1[C@H:23](C(O)=O)C[C@H:21]2[C@@H:16]1[CH2:17][CH2:18][CH2:19][CH2:20]2)=O)C)C(OCC)=O.CC(N)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([C@@H]1C[C@H:53]2[C@H:48]([CH2:49][CH2:50][CH2:51][CH2:52]2)[NH:47]1)(O)=O.C([C@@H](N[C@H](C(O)=O)C)CCC)(OCC)=O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>>[CH:48]1([N:47]=[C:23]=[N:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1

Participants

Reactant 5

HCID 8471Triethylamine

HCID 757711-Hydroxybenzotriazole

HCID 441313Perindopril Erbumine

HCID 10015159(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid

HCID 131727202(2S,3aS,7aS)-2-carboxyperhydroindole, p-toluenesulfonate salt

Product 1

HCID 10868Dicyclohexylcarbodiimide

Procedure

WO 01/58868 discloses a method for preparation of perindopril erbumine comprising reacting benzyl ester of (2S,3aS,7aS)-2-carboxyperhydroindole, p-toluenesulfonate salt with (S,S) diastereoisomer of N-[(S)-1-carbethoxybutyl]-(S)-alanine in the presence of 0.4 to 0.6 moles of 1-hydroxybenzotriazole; 1 to 1.2 moles of dicyclohexylcarbodiimide and 1 mole of triethylamine at 77° C. to give the dipeptide compound, which on debenzylation gives perindopril.

Sources & evidence

ORD record: ord-d19c382cafa745abb9ff8c511491009a
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456296B2

Linked notes

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