Benzyl succinimido carbonate → HCID 72513286, compound

HRID 1881710Notes

Reaction equation

I.[NH2:2][C:3]1[C:4]([C:11]([NH:13][C:14](=[NH:17])[S:15][CH3:16])=[O:12])=[N:5][C:6]([Cl:10])=[C:7]([NH2:9])[N:8]=1.[CH2:18]([O:25][C:26](ON1C(=O)CCC1=O)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[NH2:2][C:3]1[C:4]([C:11]([NH:13][C:14](=[N:17][C:26](=[O:27])[O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:15][CH3:16])=[O:12])=[N:5][C:6]([Cl:10])=[C:7]([NH2:9])[N:8]=1

Participants

Conditions

Temperature: 66 °C

Procedure

To a stirred solution of 1-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-2-methyl-isothiourea hydroiodide (Intermediate I) (50 g, 0.129 mol) in dry THF (1 L) is added TEA (18 mL, 0.129 mol), followed by N-(benzyloxycarbonyloxy)-succinimide (32.1 g, 0.129 mol). The reaction mixture is then heated to reflux (66° C.) for 6 hours. The reaction is allowed to cool to room temperature, then concentrated in vacuo to a yellow solid. The crude is suspended in EtOAc (500 mL) and water (500 mL) and is triturated vigorously for a period of 30 minutes. The resulting suspension is filtered and dried in a vacuum oven (40° C.) over P2O5 to give the product as a pale yellow solid. [M+H]+ 395

Workup

temperatureThe reaction mixture is then heated
temperatureto cool to room temperature
concentrationconcentrated in vacuo to a yellow solid
customwater (500 mL) and is triturated vigorously for a period of 30 minutes
filtrationThe resulting suspension is filtered
dry with materialdried in a vacuum oven (40° C.) over P2O5

Sources & evidence

ORD record: ord-cf23d8cb13e245e897fe8e0ed93d9c02
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318935B2

Reaction notes

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