Lithium hydroxide, monohydrate → HCID 67076745, compound

HRID 1348611Notes

Reaction equation

HRID 1348611 reaction equation
C([O:3][C:4](=[O:28])[C:5]([CH3:27])([CH3:26])[C:6]([NH:8][C@@H:9]1[C:15](=[O:16])[N:14]([CH2:17][CH:18]=[CH2:19])[C:13]2[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:12]=2[O:11][C@@H:10]1[CH3:25])=[O:7])C.O.[OH-].[Li+]>O1CCCC1.O>[CH2:17]([N:14]1[C:13]2[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:12]=2[O:11][C@H:10]([CH3:25])[C@H:9]([NH:8][C:6](=[O:7])[C:5]([CH3:27])([CH3:26])[C:4]([OH:28])=[O:3])[C:15]1=[O:16])[CH:18]=[CH2:19]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67077078HCID 67077078, compound

Product 1

HCID 67076745HCID 67076745, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.72 g (1.84 mmol) N-((6R,7S)-9-Allyl-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-2,2-dimethyl-malonamic acid ethyl ester in 10 ml tetrahydrofurane were treated with 0.08 g (1.84 mmol) lithium hydroxide monohydrate in 3 ml water for 5 hours at room temperature. The tetrahydrofurane was distilled off and the aqueous phase was extracted with diethylether. The water phase was acidified with 1.84 ml 1 N aqueous hydrochloric acid and extracted with ethylacetate to yield 482 mg (72%) N-((6R,7S)-9-allyl-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-2,2-dimethyl-malonamic acid as white solid, MS m/e (%): 365.0 (M+H+, 100).

Workup

  1. distillationThe tetrahydrofurane was distilled off
  2. extractionthe aqueous phase was extracted with diethylether
  3. extractionextracted with ethylacetate

Sources & evidence

ORD record
ord-43068a0900754b63b0b44ef421eda2b8
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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