1,2-Dichloroethane → Methyl-2-[4-({(2s)-2-(acetylamino)-3-[4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]propanoyl}amino)butoxy]-6-hydroxybenzoate

HRID 724593Notes

Reaction equation

Cl.[CH3:2][O:3][C:4](=[O:18])[C:5]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][NH2:17].C([O:23][C:24]([NH:26][C@@H:27]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[S:42](=[O:44])(=[O:43])[N:41](C(C)(C)C)[C:40](=[O:49])[CH:39]=2)=[CH:34][CH:33]=1)[C:28](O)=[O:29])=O)(C)(C)C.[CH2:50](Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:18])[C:5]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:28](=[O:29])[C@@H:27]([NH:26][C:24](=[O:23])[CH3:50])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[S:42](=[O:44])(=[O:43])[NH:41][C:40](=[O:49])[CH:39]=2)=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 40 °C

Procedure

21-A (Bioorg. & Medchem. Lett. (2003), 13, 3129–3132) (8 mg, 0.029 mmol) was added to a DCM (0.1 M) solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]propanoic acid (12 mg, 0.027 mmol), EDC (5 mg, 0.027 mmol), HOBt (3.6 mg, 0.027 mmol) and DIEA (10 μL, 0.029 mmol). The reaction was stirred at 40° C. for 4 h and then concentrated. The crude was purified by reverse phase HPLC to afford 21-B (8.1 mg, 44%).

Workup

concentrationconcentrated
customThe crude was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-218d758e599b4be6b5f65cd837b09be8
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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