1,2-Dichloroethane → 4-(2-Aminothiazol-4-yl)butanoyl-glycyl-2(S)-phenylsulfonamido-beta-alanine t-butyl ester

HRID 618137Notes

Reaction equation

Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[N:7]=1.FC(F)(F)C(O)=O.[C:21]([O:25][C:26](=[O:44])[C@@H:27]([NH:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH2:28][NH:29][C:30](=[O:33])[CH2:31][NH2:32])([CH3:24])([CH3:23])[CH3:22].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[C:21]([O:25][C:26](=[O:44])[C@@H:27]([NH:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH2:28][NH:29][C:30](=[O:33])[CH2:31][NH:32][C:11](=[O:13])[CH2:10][CH2:9][CH2:8][C:6]1[N:7]=[C:3]([NH2:2])[S:4][CH:5]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: -15 °C

Procedure

Acid 1-4 (300 mg, 1.35 mmol), amine 1-7 (600 mg, 1.37 mmol), HOBT (219 mg, 1.14 mmol) and NMM (445 μL, 4.04 mmol) were combined in 13 mL DMF, cooled to -15° C., and EDC (310 mg, 1.61 mmol) was added. The reaction was warmed to RT, stirred overnight, then diluted with EtOAc, washed with water, sat. NaHCO3, and brine, dried (MgSO4), filtered and concentrated. Flash chromatography (silica, 20% MeOH/EtOAc) provided 1-8 as yellow solid.

Workup

temperatureThe reaction was warmed to RT
washwashed with water, sat. NaHCO3, and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-f1d65958061f47adb2585230fd7f2675
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05952306

Reaction notes

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