Diisopropylethylamine → HCID 67384932, compound

HRID 2360979Notes

Reaction equation

HRID 2360979 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2([C:17](=[O:25])[NH:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[C:27]([O:31][C:32]([NH:34][C@@H:35]([CH2:39][C:40]1[S:41][CH:42]=[CH:43][CH:44]=1)[C:36](O)=[O:37])=[O:33])([CH3:30])([CH3:29])[CH3:28].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2([C:17](=[O:25])[NH:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:16][CH2:15][N:14]([C:36](=[O:37])[C@@H:35]([NH:34][C:32]([O:31][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:33])[CH2:39][C:40]3[S:41][CH:42]=[CH:43][CH:44]=3)[CH2:13][CH2:12]2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27344843-(Thien-2-yl)-L-alanine, N-BOC protectedHCID 67384732HCID 67384732, compound

Product 1

HCID 67384932HCID 67384932, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4-cyclohexylcarbamoyl-piperidin-4-ylmethyl)-benzoic acid methyl ester (3.32 mmol; 1.19 g) in DMF (50 mL) was added (S)-2-tert-butoxycarbonylamino-3-thiophen-2-yl-propionic acid (3.32 mmol; 0.90 g), N,N-diisopropyl-N-ethylamine (6.64 mmol; 1.18 mL) and HBTU (4.32 mmol; 1.64 g), and the resulting mixture was stirred at room temperature overnight. Ethyl acetate (150 mL) was added, and the resulting solution was washed with a 1H hydrochloric acid solution (2×50 mL), and brine (50 mL). The organic phase was dried over magnesium sulfate, filtered, and evaporated. The residue was purified via flash column chromatography (eluent gradient: 0 to 10% methanol in dichloromethane) and the desired fractions were combined and evaporated to yield 4-[1-(2-(S)-tert-butoxycarbonylamino-3-thiophen-2-yl-propionyl)-4-cyclohexylcarbamoyl-piperidin-4-ylmethyl]-benzoic acid methyl ester. MS (ESI) m/z 612.13 [M+H]+.

Workup

  1. washthe resulting solution was washed with a 1H hydrochloric acid solution (2×50 mL), and brine (50 mL)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified via flash column chromatography (eluent gradient: 0 to 10% methanol in dichloromethane)
  6. customevaporated

Sources & evidence

ORD record
ord-db47156cdc03479991e5773a18d6efb9
Source dataset
uspto-grants-2014_04
Patent number
US08686152B2

Reaction notes

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