Hydrochloric Acid → 3-{[(Tert-butoxy)carbonyl]amino}-2,2-dimethylpropanoic acid

HRID 842454Notes

Reaction equation

HRID 842454 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([CH3:17])([CH3:16])[C:11]([O:13]CC)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O.C1COCC1.Cl>CCCCCCC.C(Cl)Cl.O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([CH3:17])([CH3:16])[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 22614204Ethyl 3-((tert-butoxycarbonyl)amino)-2,2-dimethylpropanoate

Product 1

HCID 117906313-{[(Tert-butoxy)carbonyl]amino}-2,2-dimethylpropanoic acidYield 160.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Conditions

Temperature
64 °C

Procedure

Two 22 L flasks were each charged with compound 54a (583 g, 2.38 mol), LiOH.H2O (204.5 g, 4.87 mol), THF (5.7 L), and water (4.75 L). The reaction mixtures were heated to 64° C. for 19 h. The mixtures were then cooled to 10° C. with an ice bath. Approximately 1 L of 6N HCl was added to each reaction mixture to bring the pH to 3-3.5. Each mixture was combined with 2.9 L of CH2Cl2, and the aqueous layers were separated. The aqueous layers were extracted with another 1.5 L portion of CH2Cl2. The combined organic layers were dried with sodium sulfate and concentrated in vacuo to give a white solid. The solid was slurried in 5 L of heptane for 1 h, filtered, and vacuum dried to give 830 g (80% yield) of compound 55 as a white solid, mp 114-116° C. Anal. Calcd for C10H19NO4: C, 55.28; H, 8.81; N, 6.45. Found: C, 55.55; H, 8.77; N, 6.56.

Workup

  1. customThe reaction mixtures
  2. temperatureThe mixtures were then cooled to 10° C. with an ice bath
  3. customthe aqueous layers were separated
  4. extractionThe aqueous layers were extracted with another 1.5 L portion of CH2Cl2
  5. dry with materialThe combined organic layers were dried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a white solid
  8. filtrationfiltered
  9. customvacuum dried

Sources & evidence

ORD record
ord-3b55851ff27f4c908774f872fe869d6b
Source dataset
uspto-grants-2002_04
Patent number
US06376230B1

Reaction notes

Loading…