1,2-Dichloroethane → 4-[2-(Thiazol-2-ylamino)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester

HRID 583694Notes

Reaction equation

HRID 583694 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][N:4]=[C:3]1[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1.Cl.[NH2:21][CH2:22][C@H:23]([NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CCOC(C)=O.CN(C=O)C>[C:27]([O:26][C:24](=[O:25])[C@@H:23]([NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH2:22][NH:21][C:15](=[O:17])[C:14]1[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][NH:7][C:3]2[S:2][CH:6]=[CH:5][N:4]=2)=[CH:19][CH:18]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 22853534(S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochlorideHCID 867524494-[2-(Thiazol-2-ylamino)ethyloxy]benzoic acid hydrochloride

Product 1

HCID 867524504-[2-(Thiazol-2-ylamino)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acid 24-5 (160 mg, 0.60 mmol), amine 2-1 (215 mg, 0.60 mmol), EDC (140 mg, 0.73 mmol), HOBT (98 mg, 0.73 mmol), and NMM (235 μL, 2.1 mmol) were combined in 3 miL DMF at -15°. After stirring at RT for 16 h, the reaction was diluted with EtOAc, washed with water, sat. NaHCO3 and brine, dried, concentrated, and purified by flash chromatography (silica, 70% EtOAc/hexane) providing 24-6 as an off-white solid. Rf 0.54 (silica, EtOAc).

Workup

  1. washwashed with water, sat. NaHCO3 and brine
  2. customdried
  3. concentrationconcentrated
  4. custompurified by flash chromatography (silica, 70% EtOAc/hexane)

Sources & evidence

ORD record
ord-fa793f8a8f5e4cd88ee57f87b7e0a926
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

Loading…