Hydrochloric Acid → HCID 86597964, compound

HRID 349836Notes

Reaction equation

HRID 349836 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][C@@H:6]([NH:13]C(=O)C)[C@H:7]([CH3:12])[C@H:8]([CH3:11])[CH2:9][CH3:10])C.[ClH:18]>>[ClH:18].[NH2:13][C@@H:6]([C@H:7]([CH3:12])[C@H:8]([CH3:11])[CH2:9][CH3:10])[CH2:5][C:4]([OH:17])=[O:3]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86597965HCID 86597965, compound

Product 1

HCID 86597964HCID 86597964, compoundYield 89%

Procedure

(3R,4R,5R)-3-Acetylamino-4,5-dimethyl-heptanoic acid ethyl ester (13.63 g, 56.0 mmol) was heated under reflux with 200 mL of 1M hydrochloric acid for 72 hours. The solution was cooled and extracted 2× with 50 mL aliquots of MTBE. The aqueous phase was evaporated to a semisolid. Acetonitrile (4×100 mL) was added and evaporated to give 10.75 g (89% yield) of the titled compound as a white crystalline solid: 1H NMR (CD3OD, 399.77 MHz) 0.87 (t, J=7.3 Hz, 3H), 0.94 (t, J=6.6 Hz, 6H), 1.02–1.15 (m, 1H), 1.37–1.53 (m, 2H), 1.58–1.68 (m, 1H), 2.64 (dd, J=17.5, 7.4 Hz, 1H), 2.73 (dd, J+17.5, 4.8 Hz, 1H), 3.54–3.61 (m, 1H). Low resolution mass spec: nominal m/e calc'd for C9H20ClNO2 (M+H)+: 174. Found: m/e 174.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted 2× with 50 mL aliquots of MTBE
  3. customThe aqueous phase was evaporated to a semisolid
  4. additionAcetonitrile (4×100 mL) was added
  5. customevaporated

Sources & evidence

ORD record
ord-cc1ab6ffb248411bbb2ac74894e78ef2
Source dataset
uspto-grants-2007_02
Patent number
US07179934B2

Reaction notes

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