Ammonia → Ammonium L-(+)-Tartrate

HRID 2299576Notes

Reaction equation

HRID 2299576 reaction equation
[C:1]([C@@H:4]([C@H:6]([C:8]([OH:10])=[O:9])[OH:7])[OH:5])([OH:3])=[O:2].[NH2:11][C@@H]1C[C@H](C(OC)=O)C=C1.[Cl-].[NH4+:22].N.CO>C(O)C>[NH4+:11].[NH4+:22].[C:8]([O-:10])(=[O:9])[CH:6]([CH:4]([C:1]([O-:3])=[O:2])[OH:5])[OH:7]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 25517Ammonium ChlorideHCID 9857192(1S,4R)-Methyl 4-aminocyclopent-2-enecarboxylate (2R,3R)-2,3-dihydroxysuccinate

Product 1

HCID 2724224Ammonium L-(+)-Tartrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of (1S,4R)-Methyl 4-aminocyclopent-2-ene-1-carboxylate L-tartrate (10 g, 34.3 mmol) and ammonium chloride (1.85 g, 34.3 mmol) in ethanol (79 g) was added a 2M solution of ammonia in methanol (17.2 mL, 34.4 mmol). The mixture was stirred for 2 h, resulting in precipitation of the tartaric acid di-ammonium salt. The solid was removed by filtration and the filtrate was concentrated to about 10 mL. The concentrated filtrate was diluted with methyl isobutyl ketone (MIK), resulting in precipitation of (1S,4R) Methyl-4-aminocyclopent-2-ene-1-carboxylate hydrochloride. The solid was collected by filtration and dried in a vacuum oven (100 mbar) at 50° C. for 24 h.

Sources & evidence

ORD record
ord-7d75967f52a34ac29f11add39a6dfae3
Source dataset
uspto-grants-2002_12
Patent number
US06495711B2

Reaction notes

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