Methanol → Methyl 2-amino-4-phenylbutanoate--hydrogen chloride (1/1)

HRID 1906358Notes

Reaction equation

HRID 1906358 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[C:10](OC)([NH:14]C(C1C=CC=CC=1)=O)[C:11]([O-:13])=[O:12].S(Cl)([Cl:27])=O.[CH3:29]O>>[ClH:27].[CH3:29][O:13][C:11](=[O:12])[CH:10]([NH2:14])[CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 7501StyreneHCID 24386Thionyl ChlorideHCID 86741352HCID 86741352, compound

Product 1

HCID 13050176Methyl 2-amino-4-phenylbutanoate--hydrogen chloride (1/1)

Procedure

Dlα-amino-δ-phenylbutyric acid, prepared through amidoalkylation of styrene with methyl- -methoxyhippurate, according to Ben-Ishai et al (4.1 g, 0.018M) was dissolved in dry methanol, cooled in ice bath. Freshly distilled thionyl chloride (14.7 g, 0.12M) was added during 15 min. the ice bath was removed and the reaction mixture was left at room temp. for 3 days. Dry ether (400 ml) was added and the resulting hydrochloride ester precipitated (3.7 g, 88%) m.p. 153°-4°, lit. [D. Ben-Ishai, R. Moshenberg and J. Altman, Tetrahedron 33, 1533 (1977)] 150°-152°.

Workup

  1. temperaturecooled in ice bath
  2. customwas removed
  3. additionDry ether (400 ml) was added
  4. customthe resulting hydrochloride ester precipitated (3.7 g, 88%) m.p. 153°-4°, lit. [D. Ben-Ishai, R. Moshenberg and J. Altman, Tetrahedron 33, 1533 (1977)] 150°-152°

Sources & evidence

ORD record
ord-4610cb0374074ef992705743b6666c44
Source dataset
uspto-grants-1987_03
Patent number
US04652519

Reaction notes

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