Water → HCID 131713681, compound

HRID 2417873Notes

Reaction equation

HRID 2417873 reaction equation
Br[CH2:2][C:3]([N:5]1[C@H:13]([C:14]([O:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:12][C:7]2([S:11][CH2:10][CH2:9][S:8]2)[CH2:6]1)=[O:4].[CH3:30][NH:31][CH2:32][C:33](=[O:51])[CH:34]([NH:42][C:43](=[O:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[C:43]([NH:42][CH:34]([CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:33](=[O:51])[CH2:32][N:31]([CH2:2][C:3]([N:5]1[C@H:13]([C:14]([O:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:12][C:7]2([S:11][CH2:10][CH2:9][S:8]2)[CH2:6]1)=[O:4])[CH3:30])(=[O:50])[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 13657306HCID 13657306, compoundHCID 131713682HCID 131713682, compound

Product 1

HCID 131713681HCID 131713681, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the ester product from part (b) (2.4 g., 4.87 mmole), (±)-N-[3-(methylamino)-2-oxo-1-(phenylmethyl)propyl]benzamide (0.81 g., 2.43 mmole), prepared as set forth in Example 91(b), and diisopropylethylamine (0.85 ml., 4.87 mmole) in dimethylformamide (20 ml.) is stirred at room temperature overnight. The reaction mixture is poured into water (50 ml.), and extracted with ethyl acetate (3×100 ml.). The combined organic extracts are washed with saturated sodium bicarbonate, 10% potassium bisulfite, and water, dried (Na2SO4), and concentrated into a dark oily residue (2.8 g.). Flash chromatography (200 g. Merck silica gel, 10% ethyl acetate/methylene chloride, 20% methanol/ethyl acetate) affords 1.1 g. of (S)-7-[[[3-(benzoylamino-2-oxo-4-phenylbutyl]methylamino]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester as a yellow oil.

Workup

  1. customprepared
  2. extractionextracted with ethyl acetate (3×100 ml.)
  3. washThe combined organic extracts are washed with saturated sodium bicarbonate, 10% potassium bisulfite, and water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated into a dark oily residue (2.8 g.)
  6. customFlash chromatography (200 g. Merck silica gel, 10% ethyl acetate/methylene chloride, 20% methanol/ethyl acetate) affords 1.1 g

Sources & evidence

ORD record
ord-ce708c537dc343818a6d61346bc44b30
Source dataset
uspto-grants-1984_09
Patent number
US04470973

Reaction notes

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