Hydrochloric Acid → HCID 71547277, compound

HRID 2280362Notes

Reaction equation

HRID 2280362 reaction equation
[C:1]([NH:4][C@@H:5]([CH2:10][S:11][CH2:12][C:13]([N:15]1[CH2:18][C:17]([N+:22]([O-:24])=[O:23])([N+:19]([O-:21])=[O:20])[CH2:16]1)=[O:14])[C:6]([O:8]C)=[O:7])(=[O:3])[CH3:2].[Li+].[OH-].Cl>CO.O>[C:1]([NH:4][C@@H:5]([CH2:10][S:11][CH2:12][C:13]([N:15]1[CH2:18][C:17]([N+:22]([O-:24])=[O:23])([N+:19]([O-:21])=[O:20])[CH2:16]1)=[O:14])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71547278HCID 71547278, compound

Product 1

HCID 71547277HCID 71547277, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

(R)-Methyl 2-acetamido-3-(2-(3,3-dinitroazetidin-1-yl)-2-oxoethylthio)propanoate (1.02 g, 2.80 mmol) was dissolved in methanol (50 mL) with stirring and the mixture cooled to 0° C. Then, LiOH (0.5 M, 8.40 mL) was added dropwise to the reaction mixture via a syringe and the resulting yellow mixture stirred until TLC showed complete conversion (2.5 hours). Next, the reaction mixture was diluted with water, cooled to 0° C. and acidified to pH=2 with a 50% HCl solution. Then, the reaction mixture was extracted with ethyl acetate (×2) and the extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to provide a residue that was purified by column chromatography using silica gel and 30% MeOH in EtOAc as eluent to provide the title compound 625 mg (64%) as a white solid. 1H NMR (200 MHz, DMSO-d6) δ 1.85 (s, 3H), 2.81 (dd, 1H, J=8.4, 13.6 Hz), 3.04 (dd, 1H, J=4.8, 13.6 Hz), 3.33 (s, 2H), 4.41-4.35 (m, 1H), 4.80 (s, 2H), 5.13 (s, 2H), 8.20 (d, 1H, J=8.0 Hz). LC/MS (M+H=351). The purity was checked using LC/MS using Phenomenex Luna 3μ C8 (2) 100 A column using water with 0.1% TFA and acetonitrile with 0.1% as mobile phase (30-90% acetonitrile @ 1.0 mL/min). Retention time=0.60 mins; Area %=97.6%.

Workup

  1. stirringthe resulting yellow mixture stirred until TLC
  2. customconversion (2.5 hours)
  3. temperaturecooled to 0° C.
  4. extractionThen, the reaction mixture was extracted with ethyl acetate (×2)
  5. dry with materialthe extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto provide a residue that
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ee2594345c7b47f2a4d3580a8cc72696
Source dataset
uspto-grants-2015_09
Patent number
US09139519B2

Reaction notes

Loading…