Dimethylamine → HCID 59496618, compound

HRID 449490Notes

Reaction equation

HRID 449490 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:12]([OH:14])=O.[CH3:23][N:24](C)[CH:25]=O.C(N(CC)C(C)C)(C)C.CNC>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH:11]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:12]([N:24]([CH3:25])[CH3:23])=[O:14]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 15580505HCID 15580505, compound

Product 1

HCID 59496618HCID 59496618, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 3-(benzo[d]thiazol-2-yl)-2-(tert-butoxycarbonylamino)propanoic acid (0.15 g, 0.465 mmol) was combined with N,N,N′,N′-tetramethyl-o-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.21 g, 0.558 mmol), N,N-dimethylformamide (3.0 mL), N,N-diisopropylethylamine (120 μl, 0.92 mmol) and the 2 M dimethylamine in THF (1.0 mL). The reaction was stirred for 2 h., partitioned between ethyl acetate and 1 N HCl. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give the crude product as a semisolid. The product was purified by Flash chromatography on a silica gel column eluting hexane:ethyl acetate gradient to give tert-butyl 3-(benzo[d]thiazol-2-yl)-1-(dimethylamino)-1-oxopropan-2-ylcarbamate (0.13 g, 80%). Analytical LCMS (M+H)+: m/z=350.1.

Workup

  1. custompartitioned between ethyl acetate and 1 N HCl
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product as a semisolid
  6. customThe product was purified by Flash chromatography on a silica gel column
  7. washeluting hexane

Sources & evidence

ORD record
ord-30d59df306ab47eea4fbdea9530ea11d
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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