Lithium Hydroxide → HCID 178481557, compound

HRID 538065Notes

Reaction equation

HRID 538065 reaction equation
[Li+].[OH-].C[O:4][C:5]([C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][N:14]2[C:20](=[O:21])[C:19]3[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=3[N:17]([CH3:26])[C:16](=[O:27])[CH2:15]2)[CH2:9][CH2:8]1)=[O:6]>O1CCOCC1.O>[CH3:26][N:17]1[C:18]2[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=2[C:20](=[O:21])[N:14]([CH2:13][C@H:10]2[CH2:11][CH2:12][C@H:7]([C:5]([OH:6])=[O:4])[CH2:8][CH2:9]2)[CH2:15][C:16]1=[O:27]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178501105HCID 178501105, compound

Product 1

HCID 178481557HCID 178481557, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

LiOH (0.77 mmol, 0.02 g) was added to a solution of trans-4-(1-Methyl-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-ylmethyl)-cyclohexane carboxylic acid methyl ester (0.64 mmol, 0.22 g) in 1:1 dioxane/water (16 mL) at 0° C. After 1 h at 0° C. the ice bath was removed and the mixture was allowed to reach room temperature. The reaction mixture was washed with DCM (1×20 mL). To the aqueous layer HCl 2N was added until acid pH, then extract with DCM (3×15 mL). The organic layer was washed with brine dried over Na2SO4 anhydrous and the solvent was removed under reduced pressure to obtain the titled compound (0.18 g, yield 85%).

Workup

  1. customAfter 1 h at 0° C. the ice bath was removed
  2. customto reach room temperature
  3. washThe reaction mixture was washed with DCM (1×20 mL)
  4. additionTo the aqueous layer HCl 2N was added until acid pH
  5. extractionextract with DCM (3×15 mL)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4 anhydrous
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-332a0537dce64d7e882c74662dea0ba7
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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