HCID 86664514, compound → HCID 67505034, compound

HRID 868804Notes

Reaction equation

HRID 868804 reaction equation
[CH2:1]([NH:8][C:9](=[O:42])[C@@H:10]([NH:25][S:26]([C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34]([N:39]([CH3:41])[CH3:40])[CH:35]=2)[CH:30]=1)(=[O:28])=[O:27])[CH2:11][CH2:12][CH2:13][NH:14]C(=O)OCC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[NH2:14][CH2:13][CH2:12][CH2:11][C@H:10]([NH:25][S:26]([C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[C:34]([N:39]([CH3:41])[CH3:40])[CH:35]=2)[CH:30]=1)(=[O:28])=[O:27])[C:9]([NH:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:42]

Participants

4

Reactant 1

HCID 86664514HCID 86664514, compound

Product 1

HCID 67505034HCID 67505034, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the solution of (S)-benzyl 5-(benzylamino)-4-(6-(dimethylamino)naphthalene-2-sulfonamido)-5-oxopentylcarbamate (23 mg, 0.039 mmol) in methanol (5 ml) of was added Pd/C (10%) 5 mg. The reaction mixture was stirred under H2 balloon for 8 h at rt. After filtration the filtrate was evaporated in vacuo and the residue was triturated with ether repeatedly to provide (S)-5-amino-N-benzyl-2-(6-(dimethylamino)naphthalene-2-sulfonamido)pentanamide as colorless powder.

Workup

  1. filtrationAfter filtration the filtrate
  2. customwas evaporated in vacuo
  3. customthe residue was triturated with ether repeatedly

Sources & evidence

ORD record
ord-36ae09ddd42f4a77bbd0855f0692aecf
Source dataset
uspto-grants-2015_03
Patent number
US08969333B2

Reaction notes

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