Isophthalic Acid → HCID 66586958, compound

HRID 2409872Notes

Reaction equation

HRID 2409872 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=O)[CH:3]=1.CCN=C=NCCCN(C)C.Cl.C[NH:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:42][C:41]([CH3:44])([CH3:43])[O:40][C:38](=[O:39])[CH2:37][CH2:36][O:35][CH2:34][CH2:33][O:32][CH2:31][CH2:30][O:29][CH2:28][CH2:27][NH:26][C:5]([C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][CH:8]=1)[C:1]([OH:12])=[O:11])=[O:7]

Participants

6

Reactant 3

HCID 8496Isophthalic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53662991Methylamino-PEG3-t-butyl ester

Product 1

HCID 66586958HCID 66586958, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of isophthalic acid (1.7 g, 10.24 mmol, 2.98 equiv) in dichloromethane (10 mL), EDC.HCl (660 mg, 3.44 mmol, 1.00 equiv), 4-dimethylaminopyridine (420 mg, 3.44 mmol, 1.00 equiv), and tert-butyl 3-(2-(2-(2-(methylamino)ethoxy)ethoxy)ethoxy)propanoate 8b (1 g, 3.44 mmol, 1.00 equiv). The resulting solution was stirred for 2 h at room temperature. The resulting mixture was washed with 2×20 mL of water and 1×20 mL of NH4Cl (aq). The mixture was dried over sodium sulfate and concentrated under vacuum. The crude product (1 g) was purified by reverse phase chromatography with a water/methanol gradient to yield 500 mg (33%) of 3-((14,14-dimethyl-12-oxo-3,6,9,13-tetraoxapentadecyl)carbamoyl)benzoic acid. as yellow oil. 1H-NMR (300 MHz, CD3OD, ppm): δ 8.087 (s, 2H), 7.664-7.560 (m, 2H), 3.785-3.499 (m, 14H), 3.144-3.705 (m, 3H), 2.489-2.448 (m, 2H), 1.469-1.456 (s, 9H). MS (ES, m/z): 440 [M+H]+.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. washThe resulting mixture was washed with 2×20 mL of water and 1×20 mL of NH4Cl (aq)
  3. dry with materialThe mixture was dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product (1 g) was purified by reverse phase chromatography with a water/methanol gradient

Sources & evidence

ORD record
ord-5bc1404d692a4ea7b8a35075eba644b7
Source dataset
uspto-grants-2014_08
Patent number
US08815910B2

Reaction notes

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