Dimethylamine → HCID 15030061, compound

HRID 2355337Notes

Reaction equation

HRID 2355337 reaction equation
C[CH2:2][N:3]=[C:4]=NCCCN(C)C.Cl.[C:13]([O:17][C:18]([NH:20][C@@H:21]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:22](O)=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.CNC>CN(C1C=CN=CC=1)C.CN(C=O)C.C1COCC1>[CH:26]1([CH2:25][C@H:21]([NH:20][C:18](=[O:19])[O:17][C:13]([CH3:16])([CH3:15])[CH3:14])[C:22]([N:3]([CH3:4])[CH3:2])=[O:23])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

9

Reactant 5

HCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10588189(2S)-2-(((tert-butoxy)carbonyl)amino)-3-cyclohexylpropanoic acid

Product 1

HCID 15030061HCID 15030061, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Solid EDC.HCl (4.62 g, 24.1 mmol) was added to a solution of (S)-2-(tert-butoxycarbonylamino)-3-cyclohexylpropanoic acid (5.08 g, 19.0 mmol), diisopropylethylamine (10.0 mL, 57 mmol), HOBt (0.38 g, 2.8 mmol), DMAP (0.16 g, 1.3 mmol), dimethylamine (15 mL of a 2 M THF solution, 30 mmol), and anhydrous DMF (50 mL). The resultant clear light yellow solution was stirred at rt and the reaction progress was followed by LC-MS. After 5 h, the solvent was removed (50° C., 150 Torr). The residue was taken up in ether (200 mL) and washed with satd aq NaHCO3 (3×25 mL). Hexanes (100 mL) was added to the Et2O extract and this was washed with water (5×10 mL) and brine (3×10 mL), dried (Na2SO4), decanted and stripped. The crude material was purified using 40 g SiO2 with an eluent of hexanes to EtOAc. Combining appropriate fractions and removal of solvent gave (S)-tert-butyl 3-cyclohexyl-1-(dimethylamino)-1-oxopropan-2-ylcarbamate (3.85 g, 69%) as a white solid. MS ESI+ve m/z 321 (M+Na)+.

Workup

  1. customthe solvent was removed (50° C., 150 Torr)
  2. washwashed with satd aq NaHCO3 (3×25 mL)
  3. additionHexanes (100 mL) was added to the Et2O
  4. extractionextract
  5. washthis was washed with water (5×10 mL) and brine (3×10 mL)
  6. dry with materialdried (Na2SO4)
  7. customdecanted
  8. customThe crude material was purified
  9. customfractions and removal of solvent

Sources & evidence

ORD record
ord-0782720d15404d618db8182af50cf9c4
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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