Hydrochloric Acid → HCID 21940416, compound

HRID 1243156Notes

Reaction equation

HRID 1243156 reaction equation
[NH2:1][C:2]1([C:12]([OH:14])=[O:13])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.Cl[C:16]([O:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[O:17].[OH-].[Na+].Cl>C1OCCOC1>[CH2:19]([O:18][C:16]([NH:1][C:2]1([C:12]([OH:14])=[O:13])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1)=[O:17])[CH:20]([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 62365Isobutyl chloroformateHCID 2355332-Aminotetralin-2-carboxylic acid

Product 1

HCID 21940416HCID 21940416, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To an ice cooled solution of amino acid from Example 53B (248 mg, 1.3 mmol) and anhydrousl, 4-dioxane (6 mL) was added isobutyl chloroformate (0.23 mL, 1.69 mmol). The solution's pH was maintained at 11 using 2M NaOH. The reaction was allowed to warm to room temperature. After 1 hour the reaction was complete. The pH was adjusted to 2 with 2 M HCl and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to provide the titled compound as a sticky white solid (341 mg, 90%). 1H (δ, DMSO-d6): 12.45 (br s, 1H), 7.39 (s, 1H), 7.03–7.15 (m, 4H), 3.6–3.8 (m, 2H), 3.1–3.2 (m, 2H), 3.07 (d, 1H), 2.71 (br s, 1H), 2.25 (br s, 1H), 1.9–2.0 (m, 1H), 1.77–1.9 (m, 1H). MS (DCI/NH3): 292.1 (M+1), 309.2 (M+H+NH4+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-adaafad300c84c42ae1f7a866fd11795
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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