Potassium Carbonate → HCID 178454211, compound

HRID 591291Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:34](=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH:51]2[CH2:56]O[CH:54]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[O:53][CH2:52]2)(=O)=O)=CC=1>CN(C)C=O>[CH2:54]([O:53][C@H:52]1[CH2:51][C@H:56]([O:26][C:23]2[CH:24]=[CH:25][C:20]([CH2:19][C@H:11]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH2:10][C@@H:9]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:21][CH:22]=2)[CH2:34]1)[C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 349 mg (0.75 mmol) of di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-(4-hydroxy-benzyl)-L-glutamate (Example 1 b) in 15 mL NA-dimethylformamide were added 138 mg (1.0 mmol) of potassium carbonate and 332 mg (1.0 mmol) of 2-phenyl-1,3-dioxan-5-yl 4-methylbenzenesulfonate (Studii si Cercetari de Chimie (1960), 8, 187-99.) and the resulting suspension was heated for 2 h at 100° C. in a microwave oven. The reaction mixture was then filtered, the solvent evaporated and the residue was taken up in DMSO. The crude product obtained in this manner was chromatographed on a PrepCon® C-18 reversed phase column using a water/acetonitrile gradient (35/65 to 0/100), and the appropriate fractions were combined and concentrated.

Workup

filtrationThe reaction mixture was then filtered
customthe solvent evaporated

Sources & evidence

ORD record: ord-b1a48950e7fe4f98b8090e4d2e7b37d1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238631B2

Reaction notes

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