1,2-Dichloroethane → HCID 69421498, compound

HRID 970210Notes

Reaction equation

HRID 970210 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:19]([OH:21])=O)[C@@H:10]([CH3:18])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[F:37][C@H:38]1[CH2:42][CH2:41][NH:40][CH2:39]1.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[O:5]([C:6]([NH:8][C@@H:9]([C@H:10]([C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)[CH3:18])[C:19]([N:40]1[CH2:41][CH2:42][C@H:38]([F:37])[CH2:39]1)=[O:21])=[O:7])[C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 16217739(s)-3-Fluoropyrrolidine hydrochlorideHCID 69143636HCID 69143636, compound

Product 1

HCID 69421498HCID 69421498, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (βS)-N-(tert-butoxycarbonyl)4-fluoro-β-methyl-L-phenylalanine Example 1, Step E, 0.15 g, 0.51 mmol) in anhydrous DMF (2 mL) was added EDC (0.25 g, 1.33 mmol), HOBT (0.18 g, 1.33 mmol), (3S)-3-fluoropyrrolidine hydrochloride (0.18 g, 1.45 mmol) and N,N′-diisopropylethylamine (0.23 mL, 1.31 mmol). After stirring at room temperature for 12 h, the reaction was diluted with ethyl acetate. The organic phase was washed sequentially with brine, 1N hydrochloric acid and 1N aqueous sodium hydroxide solution, dried over sodium sulfate, and evaporated in vacuo to yield the crude coupled product, which was used directly for the next step.

Workup

  1. washThe organic phase was washed sequentially with brine, 1N hydrochloric acid and 1N aqueous sodium hydroxide solution
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customto yield the crude

Sources & evidence

ORD record
ord-295889f3edee482598f31d24d8b57712
Source dataset
uspto-grants-2007_12
Patent number
US07309714B2

Reaction notes

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