Hydrochloric Acid → (S)-Pyrrolidine-2-carboxylic acid ((S)-2-hydroxy-propyl)-amide hydrochloride

HRID 733317Notes

Reaction equation

HRID 733317 reaction equation
C(Cl)C[Cl:3].C1C=CC2N(O)N=NC=2C=1.[OH:15][C@@H:16]([CH3:19])[CH2:17][NH2:18].C(OC([N:27]1[CH2:31][CH2:30][CH2:29][C@H:28]1[C:32](O)=[O:33])=O)(C)(C)C.Cl>O1CCOCC1>[ClH:3].[OH:15][C@@H:16]([CH3:19])[CH2:17][NH:18][C:32]([C@@H:28]1[CH2:29][CH2:30][CH2:31][NH:27]1)=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 86583742Edc hobt

Product 1

HCID 86603946(S)-Pyrrolidine-2-carboxylic acid ((S)-2-hydroxy-propyl)-amide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound I6 was prepared by EDC/HOBT-coupling of (S)-2-hydroxy-propylamine with pyrrolidine-1,2(S)-dicarboxylic acid 1-t-butyl ester (analogous to Step A of Example I4), followed by HCl-cleavage in dioxane (Step B of Example I5). The crude salt was used as such.

Sources & evidence

ORD record
ord-d4447fc29801430397f557b00066ea83
Source dataset
uspto-grants-2009_09
Patent number
US07589091B2

Reaction notes

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