Hydrochloric Acid → HCID 11658365, compound

HRID 479048Notes

Reaction equation

HRID 479048 reaction equation
C([O:5][C:6](=[O:16])[CH2:7][C@@H:8]([CH2:14][NH2:15])[CH2:9][C@H:10]([CH3:13])[CH2:11][CH3:12])(C)(C)C.C[C@H](CC)C[C@@H]1CNC(=O)C1.Cl>>[NH2:15][CH2:14][C@@H:8]([CH2:9][C@H:10]([CH3:13])[CH2:11][CH3:12])[CH2:7][C:6]([OH:16])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 54557600HCID 54557600, compoundHCID 57180487HCID 57180487, compound

Product 1

HCID 11658365HCID 11658365, compound

Conditions

Temperature
50 °C

Procedure

The mixture of amine 117 and lactam 118 was treated with 6N HCl and the solution warmed to 50° C. for 17 hours then cooled to room temperature and concentrated. The resultant oil was subjected to ion-exchange chromatography (Dowex, strongly acidic resin) using 5% ammonium hydroxide to give a cream solid which was recrystallized from methanol/ethyl acetate to give (3S, 5R)-3-aminomethyl-5-methyl-heptanoic acid, example 10. MS, m/z (relative intensity): 174 [M+H, 100%]. Anal. Calcd for C19H19N1O2. C, 62.39; H, 11.05; N, 8.08. Found: C, 62.23; H, 11.33; N, 7.89.

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated
  3. customto give a cream solid which
  4. customwas recrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-666571e9298f410286a97cef09d50768
Source dataset
uspto-grants-2003_11
Patent number
US06642398B2

Reaction notes

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