Potassium Carbonate → Di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-(4-{[3-(tosyloxy)propyl]amino}-benzyl)-L-glutamate

HRID 591261Notes

Reaction equation

[NH2:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C@H:7]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:8][C@@H:9]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:40]1([CH3:64])[CH:45]=[CH:44][C:43]([S:46]([O:49][CH2:50][CH2:51][CH2:52]OS(C2C=CC(C)=CC=2)(=O)=O)(=[O:48])=[O:47])=[CH:42][CH:41]=1>CN(C)C=O>[C:14]([O:13][C:11]([NH:10][C@H:9]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:8][C@H:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:52][CH2:51][CH2:50][O:49][S:46]([C:43]2[CH:42]=[CH:41][C:40]([CH3:64])=[CH:45][CH:44]=2)(=[O:47])=[O:48])=[CH:33][CH:32]=1)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:12])([CH3:15])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

To 230 mg (0.5 mmol) of di-tert-butyl (4S)-4-(4-aminobenzyl)-N-(tert-butoxycarbonyl)-L-glutamate in 12 mL N,N-dimethylformamide were added 138 mg (1.0 mmol) of potassium carbonate and 385 mg (1.0 mmol) of 1,3-propanediol di-p-toluenesulfonate (Aldrich) and the resulting suspension was heated for 1 h at 100° C. in a microwave oven. The reaction mixture was then filtered, the solvent evaporated and the residue was taken up in dichloromethane. The crude product obtained in this manner was chromatographed on a Biotage® SNAP cartridge KP-NH using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

Workup

filtrationThe reaction mixture was then filtered
customthe solvent evaporated

Sources & evidence

ORD record: ord-0f2e6c9292a344198eedcf6bf95a0fe3
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238631B2

Reaction notes

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