4-Methylmorpholine → 4-(4-Chlorobutyloxy)benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butylester

HRID 265893Notes

Reaction equation

HRID 265893 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.Cl.[C:17]1([S:23]([NH:26][C@@H:27]([CH2:35][NH2:36])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CCOC(C)=O.CC#N>[C:31]([O:30][C:28](=[O:29])[C@@H:27]([NH:26][S:23]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:25])=[O:24])[CH2:35][NH:36][C:11](=[O:13])[C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:15][CH:14]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 190341754-(4-Chlorobutyloxy)benzoic acidHCID 22853534(S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochloride

Product 1

HCID 867510904-(4-Chlorobutyloxy)benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butylester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirring solution of 24-3 (250 mg, 1.1 mmol), 19-2a (368 mg, 1.1 mmol), NMM (442 mg, 4.4 mmol), and CH3CN (5 mL) at ambient temperature was treated with BOP (483 mg, 1.1 mmol). After 20 h the reaction mixture was diluted with EtOAc and then washed with H2O, sat. NaHCO3, 10% KHSO4 and brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 40% EtOAc/hexanes) gave 24-4 as a white solid. TLC Rf =0.46 (silica, 50% EtOAc/hexanes);

Workup

  1. washwashed with H2O, sat. NaHCO3, 10% KHSO4 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4ecbe887068e4629b2d2c3c4e709d415
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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