Diphenylacetic Acid → HCID 86751164, compound

HRID 2258032Notes

Reaction equation

HRID 2258032 reaction equation
[NH2:1][CH:2]([CH:7]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)[S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)[C:3]([O:5][CH3:6])=[O:4].[C:25]1([CH:31]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:32](O)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:35]1([CH:31]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:32]([NH:1][CH:2]([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[C:3]([O:5][CH3:6])=[O:4])=[O:33])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 3

HCID 8333Diphenylacetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 86751163HCID 86751163, compound

Product 1

HCID 86751164HCID 86751164, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.94 g (2.7 mmol) of (R,S; R,S)-2-amino-3-(3-methoxyphenyl)-3-(3-methoxyphenyl-sulfanyl)propionic acid, methyl ester of Example 32, 15 mL of methylene dichloride, 0.69 g (3.2 mmol) of diphenylacetic acid, 0.62 g (3.2 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDAC), and 0.02 g (0.16 mmol) of 4-dimethylaminopyridine (DMAP) is stirred at room temperature for 18 hours. The reaction solution is diluted with 100 mL of methylene dichloride, washed with 80 mL of 1N sodium hydroxide and then 80 mL of 1N hydrochloric acid, dried (magnesium sulfate), and evaporated. The residue is purified via silica gel chromatography eluting with 25% ethyl acetate-hexane to give the product as an inseparable mixture of diastereomers; wt 1.10 g (90%);

Workup

  1. washwashed with 80 mL of 1N sodium hydroxide
  2. dry with material80 mL of 1N hydrochloric acid, dried (magnesium sulfate)
  3. customevaporated
  4. customThe residue is purified via silica gel chromatography
  5. washeluting with 25% ethyl acetate-hexane
  6. customto give the product
  7. additionas an inseparable mixture of diastereomers

Sources & evidence

ORD record
ord-31ee6422a16349b099c9699fc91a7f68
Source dataset
uspto-grants-1997_08
Patent number
US05658943

Reaction notes

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