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1,2-Dichloroethane → HCID 58979489, compound

HRID 1181093
Notes
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Reaction equation

HRID 1181093 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH2:23][C:24](O)=[O:25])([CH3:7])[CH3:6])[CH3:2].[Cl-].[NH4+].C(Cl)CCl.O.O[N:36]1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:27])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH2:23][C:24](=[O:25])[NH2:36])([CH3:7])[CH3:6])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 58979077HCID 58979077, compound

Product 1

HCID 58979489HCID 58979489, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Benzyloxy-2-carboxymethyl-phenoxy)-2-methyl-propionic acid ethyl ester (500 mg, 1.34 mmol), ammonium chloride (108 mg, 2.02 mmol), EDC (3.86 mg, 2.01 mmol), and N-hydroxybenzotriazole hydrate (272 mg, 2.01 mmol) were combined in a flask and diluted with DMF (5 mL). Ethyl diisopropyl amine (0.70 mL, 4.0 mmol) was added. The solution was stirred for 18 h and partitioned between EtOAc (25 mL) and 1N HCl (10 mL). The organic layer was washed with saturated NaHCO3 solution (10 mL) then brine (10 mL), dried (Na2SO4), and concentrated. The crude product was purified by radial chromatography (hexanes/EtOAc 1/2 to 1/4) to give the title compound (430 mg, 86%).

Workup

  1. custompartitioned between EtOAc (25 mL) and 1N HCl (10 mL)
  2. washThe organic layer was washed with saturated NaHCO3 solution (10 mL)
  3. dry with materialbrine (10 mL), dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by radial chromatography (hexanes/EtOAc 1/2 to 1/4)

Sources & evidence

ORD record
ord-7b3951cbdb05470d8853b0ae52fa084b
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07282501B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes