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

HRID 459026
Notes
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Reaction equation

HRID 459026 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][CH3:20])=[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 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 693985-Aminovaleric acid hydrochloride

Product 1

HCID 184429725-[(Methoxycarbonyl)amino]pentanoic acidYield 65.9%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
0 °C

Procedure

5-Aminopentanoic acid hydrochloride (2 g, 13 mmol), and potassium carbonate (13 g, 94 mmol) were dissolved in water (30 ml) and dioxane (10 ml) then cooled to 0° C. Methyl chloroformate (5 ml, 65 mmol) was added over 30 seconds, then the mixture was stirred for 2.5 hours at 0° C. Concentrated HCl was added until the mixture became 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 (1.5 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-9f9e4cbb0d144909877185776fdc134d
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