HCID 57252745, compound → HCID 57260941, compound

HRID 1167933Notes

Reaction equation

HRID 1167933 reaction equation
C([O:5][C:6](=[O:19])[CH2:7][C@@H:8]([CH2:17][NH2:18])[CH2:9][C@H:10]([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])(C)(C)C>Cl>[NH2:18][CH2:17][C@@H:8]([CH2:9][C@H:10]([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:7][C:6]([OH:19])=[O:5]

Participants

3

Reactant 1

HCID 57252745HCID 57252745, compound

Product 1

HCID 57260941HCID 57260941, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Compound 161 (1.20 g, 4.44 mmol) was heated to 50° C. in 3N HCl (30 mL) for 4 hours. The solvent was evaporated, and the oil washed with toluene, and evaporated. The crude material was passed through an ion exchange column (Dowex 50WX8-100, strongly acidic) eluting with water, then 0.5N NH4OH. Isolate (3S,5R)-3-aminomethyl-5-methyl-decanoic acid as a white solid (0.725 g, 75%): mp=174-175° C.; 1H NMR (400 MHz, CDCl3) δ 2.83 (dd, J=12.69, 4.88 Hz, 1H), 2.70 (dd, J=13.1, 7.45 Hz, 1H), 2.08 (d, J=6.59 Hz, 2H), 1.98 (m, 1H), 1.28-1.20 (m, 1H), 1.19-1.09 (m, 2H), 0.99-0.91 (m, 2H), 0.66 (m, 6H); Ms (APCI) m/z 215 (M+, 10%), 174 (M+−41, 100%); [α]D=−5.7 (c1.025 in H2O).

Workup

  1. customThe solvent was evaporated
  2. washthe oil washed with toluene
  3. customevaporated
  4. washstrongly acidic) eluting with water

Sources & evidence

ORD record
ord-bd6b103bae8a4e988bc54c499f44a07d
Source dataset
uspto-grants-2003_09
Patent number
US06620829B2

Reaction notes

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