2-(Dimethylamino)ethanol → HCID 59293924, compound

HRID 1930784Notes

Reaction equation

HRID 1930784 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[CH2:10][CH2:11][C@H:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28]O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[OH-].[Na+]>C(#N)C>[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28][O:14][C:13](=[O:15])[C@@H:12]([NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:24]

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 14798Sodium HydroxideHCID 83589L-Glutamic acid, N-((1,1-dimethylethoxy)carbonyl)-, 5-(phenylmethyl) esterHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 59293924HCID 59293924, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of (S)-2-tert-butoxycarbonylamino-pentanedioic acid 5-benzyl ester (300 mg, 0.89 mmol) and acetonitrile (5 mL) were added 2-dimethylaminoethanol (89 μL, 0.89 mmol) and benzotriazol-1-yloxytris-(dimethylamino)-phosphonium hexafluorophosphate (390 mg, 0.89 mmol) at 0° C., which was stirred overnight at room temperature. A 1N sodium hydroxide aqueous solution was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed first with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, so s to obtain the titled compound (380 mg, purity of 77%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed first with water
  3. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-70b763bf671a48e9ae33304fbf70e3e4
Source dataset
uspto-grants-2012_05
Patent number
US08188119B2

Reaction notes

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