Acetic Acid → (1R,2R,3S,4S,5R,6R)-2-amino-3-[(3,4-dichlorobenzyl)oxy]-4-[(1-methyl-1H-1,2,4-triazol-5-yl)sulfanyl]bicyclo[3.1.0]hexane-2,6-dicarboxylic acid hydrochloride

HRID 2173002Notes

Reaction equation

C(O)(=O)C.C(OC([NH:12][C@@:13]1([C:43]([O:45]C(C)(C)C)=[O:44])[C@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[C@@H:17]([S:29][C:30]2[N:31]([CH3:35])[N:32]=[CH:33][N:34]=2)[C@@H:16]2[C@H:14]1[C@H:15]2[C:36]([O:38]C(C)(C)C)=[O:37])=O)(C)(C)C>O>[ClH:27].[NH2:12][C@@:13]1([C:43]([OH:45])=[O:44])[C@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[C@@H:17]([S:29][C:30]2[N:31]([CH3:35])[N:32]=[CH:33][N:34]=2)[C@@H:16]2[C@H:14]1[C@H:15]2[C:36]([OH:38])=[O:37]

Participants

Conditions

Temperature: 140 °C

Procedure

Add acetic acid (2.0 mL) and water (2.0 mL) to di-tert-butyl (1R,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-dichlorophenyl)methoxy]-4-[(2-methyl-1,2,4-triazol-3-yl)sulfanyl]bicyclo[3.1.0]hexane-2,6-dicarboxylate (0.305 g, 0.445 mmol) in a microwave vessel and seal and heat the mixture to 140° C. for 25 minutes. Cool and concentrate the mixture to dryness, and then add 5 N hydrochloric acid (2 mL), acetonitrile (2 mL), and transfer to a vial. Lyophilize overnight to yield the title compound as a white solid (0.227 g, 0.445 mmol; 95%): MS (m/z): 473/475/477 (M+1).

Workup

customseal
temperatureCool
concentrationconcentrate the mixture to dryness
additionadd 5 N hydrochloric acid (2 mL), acetonitrile (2 mL), and transfer to a vial

Sources & evidence

ORD record: ord-73764a30e3d54f06995283e71f7d2f4c
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056844B2

Reaction notes

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