Triethylamine → HCID 69620892, compound

HRID 1628296Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([NH:15][C:16](=[O:33])[C@@H:17]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([CH3:14])[CH:9]=2)[CH:7]=1.C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH3:14][C:10]1[CH:9]=[C:8]([C:6]2[CH:5]=[C:4]([NH:15][C:16](=[O:33])[C@@H:17]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:3]=[C:2]([NH:1][S:42]([CH3:41])(=[O:44])=[O:43])[CH:7]=2)[CH:13]=[CH:12][N:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 51.1D (512 mg, 1.16 mmol) and triethylamine (478 μl, 3.44 mmol) in CH2Cl2 (10 mL) under N2 was added methanesulfonyl chloride (available from Aldrich) (84.3 μl, 1.08 mmol) drop wise over 10 min. After stirring at 0° C. for 30 min, the reaction mixture was treated with saturated aqueous NaHCO3 (1 mL), diluted with water (10 mL), and extracted with CH2Cl2 (3×10 mL). Organic layers were combined, dried over MgSO4, and concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel using 0-70% EtOAc/CH2Cl2 provided title product 51.1E as white solid (268 mg, 43%).

Workup

extractionextracted with CH2Cl2 (3×10 mL)
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customPurification of the residue by flash chromatography on silica gel using 0-70% EtOAc/CH2Cl2

Sources & evidence

ORD record: ord-7304fb8d49a44900b78c100b2a3392af
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785468B2

Reaction notes

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