Hydrochloric Acid → HCID 86695985, compound

HRID 2173003Notes

Reaction equation

HRID 2173003 reaction equation
Cl.C(OC([NH:9][C@@:10]1([C:34]([OH:36])=[O:35])[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[C@@H:14]([NH:26][C:27](=[O:30])[CH2:28][OH:29])[C@@H:13]2[C@H:11]1[C@H:12]2[C:31]([OH:33])=[O:32])=O)(C)(C)C>O1CCOCC1.O>[ClH:24].[NH2:9][C@@:10]1([C:34]([OH:36])=[O:35])[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[C@@H:14]([NH:26][C:27](=[O:30])[CH2:28][OH:29])[C@@H:13]2[C@H:11]1[C@H:12]2[C:31]([OH:33])=[O:32]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67705253HCID 67705253, compound

Product 1

HCID 86695985HCID 86695985, compoundYield 133.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 4N hydrogen chloride (3.0 mL, 12.0 mmol) in 1,4-dioxane to a mixture of (1S,2R,3R,4S,5R,6S)-2-(tert-butoxycarbonylamino)-3-[(3,4-dichlorophenyl)methoxy]-4-[(2-hydroxyacetyl)amino]bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (0.032 g, 0.06 mmol) in water (0.3 mL). Wash the solid with acetonitrile and diethylether on a fritted funnel Sequentially wash the solid with acetonitrile and diethylether and then further dry in a vacuum oven overnight at 50° C. to provide the title compound as a white solid (0.018 g, 0.04 mmol, 65%). MS (m/z): 433 (M+H).

Workup

  1. washWash the solid with acetonitrile and diethylether on a fritted funnel
  2. washSequentially wash the solid with acetonitrile and diethylether
  3. customfurther dry in a vacuum oven overnight at 50° C.

Sources & evidence

ORD record
ord-e8cb1ab982124de99c65178efd763b1c
Source dataset
uspto-grants-2015_06
Patent number
US09056844B2

Reaction notes

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