1,3,4-Thiadiazol-2-amine → HCID 70085747, compound

HRID 2269362Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (2S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylaminohexanoic acid (1.09 g, 2.87 mmol) in dichloromethane (5 mL) is added 1,1-carbonyldiimidazole (0.47 g, 2.87 mmol). The resulting solution is stirred at 25° C. for 1 h and 2-amino-1,3,4-thiadiazole (0.29 g, 2.87 mmol) is added and the reaction is stirred for an additional 18 h. The mixture is diluted with dichloromethane (60 mL) and washed with 1 M aqueous sodium carbonate solution. The organic layer is dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by silica gel chromatography (elution with 1:1 EtOAc-hexanes) to provide (2S)-6-benzyloxycarbonylamino-2-tert-butoxycarbonylaminohexanoic acid 1,3,4-thiadiazol-2-ylamide as a foam (0.81 g, 61% yield).

Workup

stirringthe reaction is stirred for an additional 18 h
washwashed with 1 M aqueous sodium carbonate solution
dry with materialThe organic layer is dried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
custompurified by silica gel chromatography (elution with 1:1 EtOAc-hexanes)

Sources & evidence

ORD record: ord-7f102f34a43041988f9c3a6eb7a18721
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329400B1

Reaction notes

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