Hydrochloric Acid → Methyl 2-aminohex-5-enoate

HRID 1647365Notes

Reaction equation

HRID 1647365 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]([CH2:23][C:24]1[CH:29]=[CH:28]C=CC=1)[C:13](N[C@H](C(OC)=O)CO)=[O:14].Cl.O.[CH2:32]([O:34]CC)C>>[CH3:32][O:34][C:13](=[O:14])[CH:12]([CH2:23][CH2:24][CH:29]=[CH2:28])[NH2:3]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 67799768N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-L-serine, methyl ester

Product 1

HCID 15356347Methyl 2-aminohex-5-enoate

Procedure

Dissolve N-(phenylmethylene)-2-(3-butenyl)glycine methyl ester (25g) in ethyl ether (400mL) and stir with 1N hydrochloric acid (150mL) and water (150mL). Place under an argon atmosphere and stir for 2 hours. Separate the aqueous phase and adjust to pH 9, extract into chloroform, dry and evaporate the solvent in vacuo to give the title compound as a light oil (4.5g).

Workup

  1. customSeparate the aqueous phase
  2. extractionextract into chloroform
  3. customdry
  4. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-b61569c2295d41ac97c0b9dcf2601c46
Source dataset
uspto-grants-1995_07
Patent number
US05430145

Reaction notes

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