Acetic Acid → (1S,2R,3R,4S,5R,6S)-4-(Acetylamino)-2-amino-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylic acid

HRID 2173001Notes

Reaction equation

[C:1]([NH:4][C@H:5]1[C@@H:10]2[C@@H:8]([C@H:9]2[C:11]([O:13]C(C)(C)C)=[O:12])[C@:7]([NH:25]C(OC(C)(C)C)=O)([C:18]([O:20]C(C)(C)C)=[O:19])[C@@H:6]1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([Cl:42])[CH:36]=1)(=[O:3])[CH3:2].C(O)(=O)C>O>[C:1]([NH:4][C@H:5]1[C@@H:10]2[C@@H:8]([C@H:9]2[C:11]([OH:13])=[O:12])[C@:7]([NH2:25])([C:18]([OH:20])=[O:19])[C@@H:6]1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([Cl:42])[CH:36]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

Di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-(acetylamino)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (2.40 g, 3.81 mmol) is added to acetic acid (7.99 g, 7.62 mL, 133.05 mmol,) and water (3.81 mL, 3.81 g, 211.60 mmol) and heated in a microwave to 140° C. After 15 minutes, cool to room temperature, dilute with water and filter to collect the solids. Sequentially wash the solids with water (2×50 mL) and diethyl ether (2×50 mL), and then dry in a vacuum oven giving the title compound (1.23 g, 2.95 mmol, 77%): MS (m/z): 417/419 (M+1).

Workup

temperaturecool to room temperature
filtrationfilter
customto collect the solids
washSequentially wash the solids with water (2×50 mL) and diethyl ether (2×50 mL)
customdry in a vacuum oven

Sources & evidence

ORD record: ord-d6968020280247178c121ef348960578
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056844B2

Reaction notes

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