Water → HCID 57037040, compound

HRID 485191Notes

Reaction equation

HRID 485191 reaction equation
Br[CH2:2][C:3]([N:5]1[CH:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[CH3:22][NH:23][CH2:24][C:25](=[O:43])[CH:26]([NH:34][C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[C:35]([NH:34][CH:26]([CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:25](=[O:43])[CH2:24][N:23]([CH2:2][C:3]([N:5]1[C@H:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4])[CH3:22])(=[O:42])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 13657306HCID 13657306, compoundHCID 14127395HCID 14127395, compound

Product 1

HCID 57037040HCID 57037040, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(bromoacetyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, 1,1-dimethylethyl ester (2.12 g., 6 mmole) in dimethylformamide (20 ml.) is added (±)-N-[3-(methylamino)-2-oxo-1-(phenylmethyl)propyl]benzamide (2.0 g., 6 mmole), prepared as set forth in Example 91(b), and diisopropylethylamine (0.77 g., 1.04 ml., 6 mmole). The reaction mixture is stirred overnight, poured into water (50 ml.) and extracted with ethyl acetate (3×50 ml.). The combined ethyl acetate extracts are washed with saturated sodium bicarbonate (twice) and water (twice), dried (Na2SO4), and concentrated into a yellow oily residue (2.9 g.). Flash chromatography (200 g. Merck silica, 2% methanol/chloroform) gives 0.68 g. of (S)-2-[[[3-(benzoylamino)-2-oxo-4-phenylbutyl]methylamino]acetyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, 1,1-dimethylethyl ester as a yellow dried up foam.

Workup

  1. customprepared
  2. extractionextracted with ethyl acetate (3×50 ml.)
  3. washThe combined ethyl acetate extracts are washed with saturated sodium bicarbonate (twice) and water (twice),
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated into a yellow oily residue (2.9 g.)
  6. customFlash chromatography (200 g. Merck silica, 2% methanol/chloroform) gives 0.68 g
  7. dry with materialof (S)-2-[[[3-(benzoylamino)-2-oxo-4-phenylbutyl]methylamino]acetyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, 1,1-dimethylethyl ester as a yellow dried up foam

Sources & evidence

ORD record
ord-4444ef538bdf429b8d98d5b550d3d057
Source dataset
uspto-grants-1985_08
Patent number
US04535176

Reaction notes

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