Diisopropylethylamine → HCID 131724971, compound

HRID 1070436Notes

Reaction equation

HRID 1070436 reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@@:9]1([CH3:16])[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[C:18]([C:20]1[CH:39]=[CH:38][CH:37]=[CH:36][C:21]=1[O:22][C:23]1[CH:35]=[CH:34][C:26]([CH2:27][C@@H:28]([C:30]([O:32][CH3:33])=[O:31])[NH2:29])=[CH:25][CH:24]=1)#[N:19].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@@:9]1([CH3:16])[C:10]([NH:29][C@H:28]([C:30]([O:32][CH3:33])=[O:31])[CH2:27][C:26]1[CH:25]=[CH:24][C:23]([O:22][C:21]2[CH:36]=[CH:37][CH:38]=[CH:39][C:20]=2[C:18]#[N:19])=[CH:35][CH:34]=1)=[O:12])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 11206950(2S)-1-(tert-Butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acidHCID 131724972HCID 131724972, compound

Product 1

HCID 131724971HCID 131724971, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 131 mg of N-Boc-2-(S)-methyl-(L)-proline, 190 mg 4-(2-cyanophenoxy)-phenylalanine, methyl ester hydrochloride, 297 mg PyBOP, and 4 mL of methylene chloride at 0° C. was added 300 μL of diisopropylethylamine via syringe. The reactants were allowed to warm to room temperature and said reaction was run over the weekend. The reaction was then diluted with methylene chloride, washed with water, 1N hydrochloric acid), saturated sodium bicarbonate solution, and saturated salt solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The product was purified via silica gel chromatography, eluted with 80% hexane:20% acetone to yield 263 mg of the title compound.

Workup

  1. customreaction
  2. washwashed with water, 1N hydrochloric acid), saturated sodium bicarbonate solution, and saturated salt solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe product was purified via silica gel chromatography
  6. washeluted with 80% hexane

Sources & evidence

ORD record
ord-62d28609a1164034a0eaffa9b4817deb
Source dataset
uspto-grants-2005_06
Patent number
US06903075B1

Reaction notes

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