Hydrochloric Acid → HCID 57519385, compound

HRID 1640018Notes

Reaction equation

HRID 1640018 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]=[CH:4][C:3]=1[NH:17][CH2:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([O:23]C)=[O:22].[OH-].[Li+].O1CCCC1.Cl>O.CO>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:16])[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH:5]=[CH:4][C:3]=1[NH:17][CH2:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([OH:23])=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 57519384HCID 57519384, compound

Product 1

HCID 57519385HCID 57519385, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of methyl 2-((2-bromo-4-(1-tert-butoxy-1-oxopropan-2-yl)phenylamino)methyl)benzoate (4.57 g, 10.2 mmol), lithium hydroxide (0.733 g, 30.6 mmol), tetrahydrofuran (100 mL), methanol (20 mL), and water (30 mL) was stirred overnight. The mixture was poured into water (200 mL) and the whole was acidified with 2 N HCl. The mixture was then extracted with ethyl acetate (150 mL) and the organic layer was washed with brine (100 mL), dried over sodium sulfate, and filtered. Evaporation of the solvents and drying under reduced pressure gave 2-((2-bromo-4-(1-tert-butoxy-1-oxopropan-2-yl)phenylamino)methyl)benzoic acid (4.40 g, 99%) as a thick oil: 1H NMR (500 MHz, CDCl3) δ 8.14 (d, J=7.6 Hz, 1H), 7.53 (m, 2H), 7.38 (m, 2H), 7.03 (dd, J=8.4,2.0 Hz, 1H), 6.53 (d, J=8.0 Hz, 1H), 4.80 (s, 2H), 3.44 (q, J=7.1 Hz, 1H), 1.39 (s, 9H), 1.38 (d, J=7.2 Hz, 3H).

Workup

  1. extractionThe mixture was then extracted with ethyl acetate (150 mL)
  2. washthe organic layer was washed with brine (100 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customEvaporation of the solvents
  6. customdrying under reduced pressure

Sources & evidence

ORD record
ord-cf707203dab84f3c89623e7c8df36699
Source dataset
uspto-grants-2012_02
Patent number
US08110681B2

Reaction notes

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