Benzenesulfonamide → HCID 71179013, compound

HRID 1746834Notes

Reaction equation

HRID 1746834 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:22](O)=[O:23])[CH2:10][CH2:11][C:12]([O:14]CC1C=CC=CC=1)=[O:13])=[O:7])([CH3:4])[CH3:3].C1(N=C=NC2CCCCC2)CCCCC1.[C:40]1([S:46]([NH2:49])(=[O:48])=[O:47])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[H][H]>CN(C)C1C=CN=CC=1.C(Cl)Cl.[Pd].CO>[C:2]([O:5][C:6]([NH:8][C@H:9]([C:22](=[O:23])[NH:49][S:46]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)(=[O:48])=[O:47])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:7])([CH3:3])([CH3:4])[CH3:1]

Participants

9

Reactant 4

HCID 7370BenzenesulfonamideHCID 10868DicyclohexylcarbodiimideHCID 83589L-Glutamic acid, N-((1,1-dimethylethoxy)carbonyl)-, 5-(phenylmethyl) esterHCID 178418361HCID 178418361, compound

Product 1

HCID 71179013HCID 71179013, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1.7 g (5.0 mmol) of Boc-Glu (OBzl)-OH, 1.03 g (5.0 mmol) of dicyclohexylcarbodiimide and 611 mg (5.0 mmol) of 4-(dimethylamino)pyridine were suspended in 20 ml of methylene chloride, to which 866 mg (5.0 mmol) of benzenesulfonamide was added. Following agitation at room temperature overnight, extraction was performed with ethyl acetate/1N hydrochloric acid. The organic layer was washed with saturated saline and then added with sodium sulfate for drying. The organic layer was subjected to vacuum condensation. To the resulting residue, 100 mg of 10% Pd/C and 20 ml of methanol were added and stirred overnight in a hydrogen atmosphere under a normal pressure. After filtrating the catalyst away, the solvent was distilled away and purification step A was used to obtain a crude product of the title compound.

Workup

  1. additionwas added
  2. customat room temperature
  3. extractionovernight, extraction
  4. washThe organic layer was washed with saturated saline
  5. additionadded with sodium sulfate
  6. customfor drying
  7. customThe organic layer was subjected to vacuum condensation
  8. filtrationAfter filtrating the catalyst away
  9. distillationthe solvent was distilled away
  10. custompurification step A

Sources & evidence

ORD record
ord-f7b0b4c88db4403cb69b5d50aff1feab
Source dataset
uspto-grants-2015_10
Patent number
US09150505B2

Reaction notes

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