HCID 178454295, compound → HCID 178454294, compound

HRID 1497499Notes

Reaction equation

HRID 1497499 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[N:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[NH:10][C:11]1[CH:37]=[CH:36][C:14]([C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27]CC3C=CC=CC=3)=[O:26])=[CH:20][C:19]=2[Cl:35])=[O:16])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.[C].[Pd]>[C:42]([O:41][C:39]([NH:38][C:9](=[N:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[NH:10][C:11]1[CH:37]=[CH:36][C:14]([C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:20][C:19]=2[Cl:35])=[O:16])=[CH:13][CH:12]=1)=[O:40])([CH3:44])([CH3:45])[CH3:43]

Participants

4

Reactant 1

HCID 178454295HCID 178454295, compound

Product 1

HCID 178454294HCID 178454294, compoundYield 104.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[2-(benzyloxy)-2-oxoethyl]-2-chlorophenyl 4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoate (1.98 g) in tetrahydrofuran (27.1 mL) was added 10% palladium-carbon (196 mg), followed by stirring at room temperature for 1 hour at normal pressure under a hydrogen atmosphere. The reaction suspension was filtered through Celite, and then the filtrate was concentrated under reduced pressure to obtain [4-({4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoyl}oxy)-3-chlorophenyl]acetic acid (1.78 g).

Workup

  1. filtrationThe reaction suspension was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d40e378594ff41d7ba986508dad46277
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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