Dimethylformamide → Tert-butyl (2S)-3-amino-2-benzenesulfonamidopropanoate

HRID 265894Notes

Reaction equation

HRID 265894 reaction equation
[C:1]([O:5][C:6](=[O:34])[C@@H:7]([NH:24][S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:8][NH:9]C(=O)C1C=CC(OCCCCCl)=CC=1)([CH3:4])([CH3:3])[CH3:2].N1CCOCC1.CN(C=O)C>CCOC(C)=O>[C:1]([O:5][C:6](=[O:34])[C@@H:7]([NH:24][S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:8][NH2:9])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8083MorpholineHCID 867510904-(4-Chlorobutyloxy)benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butylester

Product 1

HCID 10804181Tert-butyl (2S)-3-amino-2-benzenesulfonamidopropanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirring solution of 24-4 (500 mg, 1.0 mmol), morpholine (437 gL, 5.0 mmol), and DMF (5 mL) was heated at 80° C. for 20 hours. The cooled reaction mixture was diluted with EtOAc and then washed with H2O and brine, dried (MgSO4) and concentrated. Flash chromatography (silica, EtOAc) gave 24-5 as a yellow solid. TLC Rf 0.14 (silica, EtOAc);

Workup

  1. customThe cooled reaction mixture
  2. washwashed with H2O and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b49c10adaa87459da85df6c54ad2374a
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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