Acetic Acid → HCID 69669868, compound

HRID 469918Notes

Reaction equation

C(OC([NH:8][C@@:9]1([C:32]([O:34]C(C)(C)C)=[O:33])[C@H:14]([CH2:15][S:16][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[C@@H:13]([OH:24])[C@@H:12]2[C@H:10]1[C@H:11]2[C:25]([O:27]C(C)(C)C)=[O:26])=O)(C)(C)C.O.C(O)(=O)C>>[NH2:8][C@@:9]1([C:32]([OH:34])=[O:33])[C@H:14]([CH2:15][S:16][C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[C@@H:13]([OH:24])[C@@H:12]2[C@H:10]1[C@H:11]2[C:25]([OH:27])=[O:26]

Participants

Reactant 3

HCID 176Acetic Acid

HCID 962Water

HCID 67685323HCID 67685323, compound

Product 1

HCID 69669868HCID 69669868, compoundYield 89.6%

Conditions

Temperature: 140 °C

Procedure

Di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-3-(p-tolylsulfanylmethyl)bicyclo[3.1.0]hexane-2,6-dicarboxylate (300 mg, 545.73 μmol) is placed in a microwave vial. To the vial is added water (2 mL, 110 mmol), and acetic acid (2 mL, 34.9 mmol). The mixture is heated in the microwave to 140° C. for 20 minutes. The solvent is removed under reduced pressure to give the title compound (165 mg, 489.04 μmol, 89.6%). MS (m/z): 338.0 (M+H).

Workup

customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-faa96a9288304ac99b67d5500bc58010
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629169B2

Reaction notes

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