Hydrochloric Acid → HCID 86695986, compound

HRID 2173004Notes

Reaction equation

HRID 2173004 reaction equation
C(OC([NH:8][C@@:9]1([C:37]([O:39][CH2:40][O:41][C:42]([O:44][CH:45]([CH3:47])[CH3:46])=[O:43])=[O:38])[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[C@@H:13]([OH:25])[C@@H:12]2[C@H:10]1[C@H:11]2[C:26]([O:28][CH2:29][O:30][C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])=[O:27])=O)(C)(C)C.Cl.O1CCOCC1>>[ClH:23].[NH2:8][C@@:9]1([C:37]([O:39][CH2:40][O:41][C:42]([O:44][CH:45]([CH3:47])[CH3:46])=[O:43])=[O:38])[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[C@@H:13]([OH:25])[C@@H:12]2[C@H:10]1[C@H:11]2[C:26]([O:28][CH2:29][O:30][C:31]([O:33][CH:34]([CH3:35])[CH3:36])=[O:32])=[O:27]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67704268HCID 67704268, compound

Product 1

HCID 86695986HCID 86695986, compoundYield 95%

Procedure

Add bis({[(1-methylethoxy)carbonyl]oxy}methyl) (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate in a 4.0M solution of hydrogen chloride in dioxane (14.47 mL, 57.87 mmol) and stir for 45 minutes. Add ethyl acetate, and concentrate the reaction mixture to a foam. Triturate the foam with ethyl acetate to produce a solid. Concentrate and dry under vacuum at 40° C. overnight to provide the title compound as an off-white solid (1.77 g, 2.75 mmol, 95%): MS (m/z): 608 (M+H).

Workup

  1. concentrationAdd ethyl acetate, and concentrate the reaction mixture to a foam
  2. customTriturate the foam with ethyl acetate
  3. customto produce a solid
  4. concentrationConcentrate
  5. customdry under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-e42181d97e03410f94b54c8da8dc2a46
Source dataset
uspto-grants-2015_06
Patent number
US09056844B2

Reaction notes

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