Water → HCID 131732995, compound

HRID 2176725Notes

Reaction equation

HRID 2176725 reaction equation
[CH2:1]([CH:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:6](Cl)=[O:7])[CH2:2][CH2:3][CH3:4].N[C:16]1[CH:17]=[C:18]([C:26]([O:28]C)=[O:27])[CH:19]=[C:20](C=1)[C:21]([O:23]C)=[O:22].C([N:32]([CH2:35][CH3:36])CC)C.O.O1CCC[CH2:39]1>>[CH3:16][C:17]1[C:18]([C:26]([OH:28])=[O:27])=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[C:36]([CH3:39])[C:35]=1[NH:32][C:6](=[O:7])[CH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 66831Dimethyl 5-aminoisophthalateHCID 223414352-Butyloctanoyl chloride

Product 1

HCID 131732995HCID 131732995, compound

Procedure

A solution of 2-butyloctanoyl chloride from Step 1 in dry tetrahydrofuran (50 mL) was slowly added dropwise to another solution of dimethyl 5-aminoisophthalate (Aldrich Chemical Co., 11.08 g, 53.0 mmol) and triethyl amine (11.0 mL, 78.9 mmol) in tetrahydrofuran (250 mL) under an inert atmosphere at 0° C. The mixture was then allowed to warm slowly to room temperature and was stirred overnight. Deionized water (10 mL) was added and the tetrahydrofuran was removed by rotary evaporation. The crude residue was then dissolved in 200 mL of diethyl ether, and was washed successively with saturated sodium bicarbonate (60 mL), deionized water (60 mL), and brine (60 mL). The organic phase was then dried over sodium sulfate and filtered before removing the diethyl ether by rotary evaporation. Crude dimethyl 5-(2-butyloctanamido)isophthalic acid (21.71 g) was obtained as an amber oil after drying in vacuo.

Workup

  1. customthe tetrahydrofuran was removed by rotary evaporation
  2. dissolutionThe crude residue was then dissolved in 200 mL of diethyl ether
  3. washwas washed successively with saturated sodium bicarbonate (60 mL), deionized water (60 mL), and brine (60 mL)
  4. dry with materialThe organic phase was then dried over sodium sulfate
  5. filtrationfiltered
  6. custombefore removing the diethyl ether
  7. customby rotary evaporation

Sources & evidence

ORD record
ord-385fc9c11f4d4eafbba4cf5f3d58c8e3
Source dataset
uspto-grants-2015_06
Patent number
US09067878B2

Reaction notes

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