2-(Dimethylamino)ethanol → HCID 9870903, compound

HRID 2185927Notes

Reaction equation

HRID 2185927 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:48][N:49]([CH2:51][CH2:52]O)[CH3:50].N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([S:17]([N:16]([CH2:52][CH2:51][N:49]([CH3:50])[CH3:48])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][CH2:8][CH2:7][O:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:28][CH:27]=2)(=[O:18])=[O:19])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 15462816HCID 15462816, compound

Product 1

HCID 9870903HCID 9870903, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 1 (10.71 g), triphenylphosphine (9.63 g), and dimethylaminoethanol (3.27 g) were dissolved in tetrahydrofuran (60 ml). To the resultant solution diisopropyl azodicarboxylate (7.43 g) was added dropwise over 30 min with stirring on ice. After completion of dropwise addition of the solution, the mixture was further stirred for one hour at room temperature and the solvent was removed under reduced pressure. The residue was purified through two steps: NH silica gel column chromatography (solvent=hexane:ethyl acetate=3:1,) and silica gel column chromatography (solvent=hexane:ethyl acetate=1:1 and chloroform:methanol=10:1). The resultant product was re-crystallized from ether-hexane, to thereby obtain the target product (7.42 g) in the form of crystals. Mp.: 99° C.; 1H-NMR(270 MHz, CDCl3) δ: 7.65 (2H, d, J=8.58 Hz), 7.41 (2H, d, J=8.58 Hz), 7.25 (2H, d, J=8.91 Hz), 7.18 (1H, m), 6.87 (2H, d, J=8.91 Hz), 6.72 (1H, d, J=8.25 Hz), 6.47 (2H, m), 5.78 (1H, brs), 4.08 (3H, m), 3.51 (2H, m), 3.12 (1H, m), 2.42 (1H, m), 2.22 (1H, m), 2.20 (6H, s).

Workup

  1. additionAfter completion of dropwise addition of the solution
  2. stirringthe mixture was further stirred for one hour at room temperature
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified through two steps
  5. customThe resultant product was re-crystallized from ether-hexane

Sources & evidence

ORD record
ord-e8f91a49dbcc4c79bc8b09eadb7a940d
Source dataset
uspto-grants-2002_06
Patent number
US06403607B1

Reaction notes

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