Aniline → HCID 57153549, compound

HRID 648825Notes

Reaction equation

HRID 648825 reaction equation
Br[CH2:2][C:3]([N:5]1[CH2:16][CH2:15][CH2:14][C@H:6]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:4].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1CCC[C@H]1C(OC(C)(C)C)=O>O1CCCC1.C(OCC)(=O)C>[C:18]1([NH:17][CH2:2][C:3]([N:5]2[CH2:16][CH2:15][CH2:14][C@H:6]2[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:4])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 57090629HCID 57090629, compound

Product 1

HCID 57153549HCID 57153549, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(bromoacetyl)-L-proline, 1,1-dimethylethyl ester (2.1 g., 7.5 mmole) in distilled tetrahydrofuran (40 ml.) is added aniline (1.5 g., 15 mmole) and the reaction mixture is stirred overnight under nitrogen. The reaction mixture is diluted with ethyl acetate (200 ml.), washed with saturated sodium bicarbonate (2×50 ml.) and water (twice), dried (Na2SO4), and concentrated in vacuo into a dark oily residue (4.0 g.). Flash chromatography (LPS-1 silica gel, 10% ethyl acetate/methylene chloride) affords 2.2 g. of 1-N-phenylglycyl)-L-proline, 1,1-dimethylethyl ester as a dark oil which solidifies upon drying in high vacuum.

Workup

  1. washwashed with saturated sodium bicarbonate (2×50 ml.) and water (twice),
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo into a dark oily residue (4.0 g.)
  4. customFlash chromatography (LPS-1 silica gel, 10% ethyl acetate/methylene chloride) affords 2.2 g
  5. customupon drying in high vacuum

Sources & evidence

ORD record
ord-b436a014f1da410db2a07194093301f6
Source dataset
uspto-grants-1988_04
Patent number
US04736066

Reaction notes

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