2-(Dimethylamino)ethanol → HCID 86588232, compound

HRID 1814339Notes

Reaction equation

HRID 1814339 reaction equation
[C:1]([O:5][C:6](=[O:39])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1[OH:38])(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].[CH3:40][N:41]([CH2:43][CH2:44]O)[CH3:42].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6](=[O:39])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][CH2:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1[O:38][CH2:44][CH2:43][N:41]([CH3:42])[CH3:40])(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 865882313-{2-[2-(2-hydroxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Product 1

HCID 86588232HCID 86588232, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{2-[2-(2-Hydroxy-naphthalen-1-yl)-ethoxy]-benzenesulfonylamino}-N-methoxy-N-methyl-succinamic acid tert-butyl ester (176 mg, 0.32 mmol) was combined with dimethylamino ethanol (0.063 mL, 0.63 mmol), triphenyl phosphine (165 mg, 0.63 mmol), and diethylazodicarboxylate (0.10 mL, 0.63 mmol) in freshly distilled THF (1.6 mL). The reaction was stirred at room temperature for eighteen hours. TLC analysis (silica, 50% EtOAc/hexanes) indicated consumption of the starting naphthol. The reaction mixture was concentrated and purified by gradient elution flash chromatography (SiO2, 30% EtOAc/hexanes to 50% EtOAc/hexanes to 80% EtOAc/hexanes to 100% EtOAc to 10% MeOH/CH2Cl2) to give 3-(2-{2-[2-(2-dimethylamino-ethoxy)-naphthalen-1-yl]-ethoxy}-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (75 mg, 0.12 mmol) in 38% yield. MS (APCI) m/z 630.2 (M+1).

Workup

  1. customconsumption of the starting naphthol
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by gradient elution flash chromatography (SiO2, 30% EtOAc/hexanes to 50% EtOAc/hexanes to 80% EtOAc/hexanes to 100% EtOAc to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0e4d3dabba7444e293818c6b44693b2b
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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