Glutaric anhydride → 5-{[(3-bromo-4-fluorophenyl)methyl]amino}-5-oxopentanoic Acid

HRID 657384Notes

Reaction equation

HRID 657384 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.Cl.[Br:10][C:11]1[CH:12]=[C:13]([CH2:18][NH2:19])[CH:14]=[CH:15][C:16]=1[F:17].C(N(C(C)C)CC)(C)C>C1COCC1>[Br:10][C:11]1[CH:12]=[C:13]([CH2:18][NH:19][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8])[CH:14]=[CH:15][C:16]=1[F:17]

Participants

5

Reactant 3

HCID 7940Glutaric anhydrideHCID 81531DiisopropylethylamineHCID 27249011-(3-Bromo-4-fluorophenyl)methanamine hydrochloride

Product 1

HCID 578198715-{[(3-bromo-4-fluorophenyl)methyl]amino}-5-oxopentanoic AcidYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of glutaric anhydride (342 mg, 3 mmol), [(3-bromo-4-fluorophenyl)methyl]amine hydrochloride salt (721.5 mg, 3 mmol), and diisopropyl ethyl amine (2 mL) in THF (50 mL) was stirred at room temperature for 1 hour. It was concentrated, mixed with 4% HCl (50 mL) and extracted with EtOAc (50 mL, 2×). The combined organic extracts were dried and concentrated to provide the captioned product (920 mg).

Workup

  1. concentrationIt was concentrated
  2. additionmixed with 4% HCl (50 mL)
  3. extractionextracted with EtOAc (50 mL, 2×)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-90605323a46a45d5b84f73b3495cc48b
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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