HCID 178454290, compound → HCID 178454291, compound

HRID 1497508Notes

Reaction equation

HRID 1497508 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[N:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[NH:10][C:11]1[CH:49]=[CH:48][C:14]([C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH:27][C@H:28]([C:37]([O:39]CC3C=CC=CC=3)=[O:38])[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=3)=[O:26])=[C:20]([Cl:47])[CH:19]=2)=[O:16])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.Cl.[C].[Pd]>[C:54]([O:53][C:51]([NH:50][C:9](=[N:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH:27][C@H:28]([C:37]([OH:39])=[O:38])[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=3)=[O:26])=[C:20]([Cl:47])[CH:19]=2)=[O:16])=[CH:48][CH:49]=1)=[O:52])([CH3:56])([CH3:57])[CH3:55]

Participants

5

Reactant 1

HCID 178454290HCID 178454290, compound

Product 1

HCID 178454291HCID 178454291, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl N-{[4-({4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoyl}oxy)-2-chlorophenyl]acetyl}-3-fluoro-L-phenylalaninate (260 mg) in tetrahydrofuran (4.00 mL) was added one drop of 1 M hydrochloric acid, and 10% palladium-carbon (20.5 mg) was added under an argon atmosphere, followed by stirring at room temperature for 1 hour at normal pressure under a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to obtain N-{[4-({4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoyl}oxy)-2-chlorophenyl]acetyl}-3-fluoro-L-phenylalanine (187 mg).

Workup

  1. additionwas added under an argon atmosphere
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-891630bb1dc341d78cfb1cc24127ef98
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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