Lithium hydroxide, monohydrate → HCID 69043616, compound

HRID 1372950Notes

Reaction equation

HRID 1372950 reaction equation
C([O:3][C:4](=[O:31])[C@:5]([F:30])([CH3:29])[C:6]([NH:8][C@@H:9]1[C:15](=[O:16])[N:14]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:13]2[CH:21]=[CH:22][CH:23]=[CH:24][C:12]=2[C:11]2[CH:25]=[CH:26][CH:27]=[CH:28][C:10]1=2)=[O:7])C.O.[OH-].[Li+]>O1CCCC1.O>[CH:18]1([CH2:17][N:14]2[C:15](=[O:16])[C@@H:9]([NH:8][C:6](=[O:7])[C@@:5]([F:30])([CH3:29])[C:4]([OH:31])=[O:3])[C:10]3[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=3[C:12]3[CH:24]=[CH:23][CH:22]=[CH:21][C:13]2=3)[CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69039501(S)-N-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-fluoro-2-methyl-malonamic acid ethyl ester

Product 1

HCID 69043616HCID 69043616, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.22g (0.52 mmol) (S)-N-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-fluoro-2-methyl-malonamic acid ethyl ester in 3 ml tetrahydrofurane was reacted with a solution of 0.02 g (0.52 mmol) lithium hydroxide monohydrate in 1 ml water at room temperature for 2 hours. Evaporation of the tetrahydrofurane, extraction with diethylether, acidification with 0.5 ml 1 N aqueous hydrochloric acid and extraction with ethylacetate gave 0.18 g (S)-N-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-fluoro-2-methyl-malonamic acid as white solid.

Workup

  1. customEvaporation of the tetrahydrofurane, extraction with diethylether, acidification
  2. extractionwith 0.5 ml 1 N aqueous hydrochloric acid and extraction with ethylacetate

Sources & evidence

ORD record
ord-a01b21ace23e4374b6d7304aee0dbd7e
Source dataset
uspto-grants-2007_01
Patent number
US07160875B2

Reaction notes

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