Dimethylamine → (S)-tert-butyl 1-(dimethylamino)-3-(4-isopropoxyphenyl)-1-oxopropan-2-ylcarbamate

HRID 449476Notes

Reaction equation

HRID 449476 reaction equation
F[P-](F)(F)(F)(F)F.[CH3:8][N+:9](C)=[C:10](N(C)C)ON1C2N=CC=CC=2N=N1.[C:25]([O:29][C:30]([NH:32][C@@H:33]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH:45]([CH3:47])[CH3:46])=[CH:40][CH:39]=1)[C:34](O)=[O:35])=[O:31])([CH3:28])([CH3:27])[CH3:26].C(N(CC)C(C)C)(C)C.CNC.O1CCCC1>CN(C)C=O>[CH3:8][N:9]([CH3:10])[C:34](=[O:35])[C@@H:33]([NH:32][C:30](=[O:31])[O:29][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH:45]([CH3:47])[CH3:46])=[CH:40][CH:39]=1

Participants

7

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18601565N-Boc-O-isopropyl-L-tyrosine

Product 1

HCID 59496693(S)-tert-butyl 1-(dimethylamino)-3-(4-isopropoxyphenyl)-1-oxopropan-2-ylcarbamateYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (88 mg, 0.23 mmol) was added to a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-isopropoxyphenyl)propanoic acid (50 mg, 0.2 mmol) in N,N-dimethylformamide (5 mL) and N,N-diisopropylethylamine (54 uL, 0.31 mmol). The reaction was stirred for 10 min, and the 2.00 M of dimethylamine in tetrahydrofuran (0.4 mL, 0.6 mmol) was added. The reaction was stirred for 2 h. at r.t. and was partitioned between water and ethyl acetate. The organic phase was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product, (S)-tert-butyl 1-(dimethylamino)-3-(4-isopropoxyphenyl)-1-oxopropan-2-ylcarbamate (50 mg, 90%). Analytical LCMS (M+H-Boc)+: m/z=251.0.

Workup

  1. stirringThe reaction was stirred for 2 h. at r.t.
  2. customwas partitioned between water and ethyl acetate
  3. washThe organic phase was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-77cf213b5ff2452a838447b44934a81d
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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