Hydrochloric Acid → 4-{3-Tert-butoxy-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}benzoic acid

HRID 1919899Notes

Reaction equation

HRID 1919899 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH:7]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O([Si](C)(C)C)[K].[Cl-].[NH4+].Cl>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:27])[CH:7]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 57611911Methyl 4-{3-tert-butoxy-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}benzoateHCID 178504318HCID 178504318, compound

Product 1

HCID 576119174-{3-Tert-butoxy-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}benzoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-{3-tert-butoxy-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}benzoate (0.40 g, 1.05 mmol) was dissolved in THF (10 mL). KOSiMe3 (0.27 g, 2.10 mmol) was added to the solution and allowed to stir overnight at room temperature under nitrogen. Saturated ammonium chloride was added and allowed to stir. Hydrochloric acid (2 mL, 1M solution) was added. The reaction was diluted with ethyl acetate and separated. The aqueous layer was extracted three times with ethyl acetate. The combined organic layer was dried with sodium sulfate, filtered, and concentrated. The resulting material was purified by HPLC. MS: cal'd 365 (MH+), exp 388 (MH+).

Workup

  1. stirringto stir
  2. customseparated
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. dry with materialThe combined organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting material was purified by HPLC

Sources & evidence

ORD record
ord-e37f55ae093d4de7840b0ffd3b575365
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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