1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-piperidine-1-carboxylate

HRID 1406855Notes

Reaction equation

HRID 1406855 reaction equation
[NH4+].[Cl-].C1C=CC2N(O)N=[N:9]C=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[CH2:33]([O:40][N:41]([C@H:54]1[CH2:59][N:58]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[C@H:57]([C:67](O)=[O:68])[CH2:56][CH2:55]1)[S:42]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[N+:51]([O-:53])=[O:52])(=[O:44])=[O:43])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C.CCOC(C)=O>[CH2:33]([O:40][N:41]([C@H:54]1[CH2:59][N:58]([C:60]([O:62][C:63]([CH3:64])([CH3:65])[CH3:66])=[O:61])[C@H:57]([C:67](=[O:68])[NH2:9])[CH2:56][CH2:55]1)[S:42]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[N+:51]([O-:53])=[O:52])(=[O:44])=[O:43])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86700669(2S,5R)-5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-1-(tert-butoxycarbonyl) piperidine-2-carboxylic acid

Product 1

HCID 86700668(2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-piperidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

NH4Cl (1.39 g, 26.18 mmol), HOBt (3.53 g, 26.18 mmol), EDCI (5 g, 26.18 mmol), and DIPEA (8.44 g, 65.45 mmol) were added to a solution of (2S,5R)-5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (10 g, 18.7 mmol) in DMF (90 mL) The mixture was stirred at rt for 17 hrs, then, EtOAc (500 mL) was added. he mixture was washed with saturated sodium chloride (6×), dried over Na2SO4, and concentrated. The residue was washed with petroleum ether/EtOAc (95:5, 200 mL) to give (2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-carbamoylpiperidine-1-carboxylate (9.9 g, 99%) which was used in the next step. ESI-MS (EI+, m/z): 535.0 [M+H]+.

Workup

  1. washhe mixture was washed with saturated sodium chloride (6×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. washThe residue was washed with petroleum ether/EtOAc (95:5, 200 mL)

Sources & evidence

ORD record
ord-b052afa8ef66426dbfd55b1d77059f32
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

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