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Hydrochloric Acid → 5-[(Methoxycarbonyl)amino]pentanoic acid

HRID 459042
Notes
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Reaction equation

HRID 459042 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:17]([O:19][CH2:20]C)=[O:18].Cl>O.O1CCOCC1>[CH3:20][O:19][C:17]([NH:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 693985-Aminovaleric acid hydrochloride

Product 1

HCID 184429725-[(Methoxycarbonyl)amino]pentanoic acidYield 94%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
2×
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

5-aminopentanoic acid hydrochloride (1 g, 6.5 mmol), and potassium carbonate (6.5 g, 47 mmol) were dissolved in water (15 ml) and dioxane (5 ml) then cooled to 0° C. Ethyl chloroformate (3 ml, 31.5 mmol) was added over 30 seconds, then the mixture was stirred for 4 hours at 0° C. Conc. HCl was added until acidic then the mixture was diluted with water and extracted with ether. The organic layer was dried over magnesium sulfate, evaporated and dried in vacuo to give 5-[(methoxycarbonyl)amino]pentanoic acid as a white powder (1.07 g).

Workup

  1. extractionextracted with ether
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5bee31f65f5c435a90e4283a8a234e45
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07192974B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes