Lithium Hydroxide → HCID 178485955, compound

HRID 538071Notes

Reaction equation

HRID 538071 reaction equation
[Li+].[OH-:2].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])[CH2:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[N:16]([CH3:26])[C:15]2=[O:27])[CH2:9][CH2:8]1)=[O:6]>O1CCOCC1.O>[C:15]([N:16]([CH3:26])[C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[CH2:19][C:20]([NH:14][CH2:13][C@H:10]1[CH2:11][CH2:12][C@H:7]([C:5]([OH:4])=[O:6])[CH2:8][CH2:9]1)=[O:21])([OH:27])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178501108HCID 178501108, compound

Product 1

HCID 178485955HCID 178485955, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

LiOH (1.3 mmol, 0.03 g) was added to a solution of trans-4-(1-Methyl-2,4-dioxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-ylmethyl)-cyclohexane carboxylic acid methyl ester (0.84 mmol, 0.29 g) in dioxane (3 mL) and water (3 mL) at 0° C. The mixture was stirred at 0° C. for 2 h. The reaction mixture was washed with DCM, then HCl (1N) was added until reached pH 1, then extract with DCM (3×10 mL) and AcOEt (3×10 mL). The organic layers were washed with brine (2×10 mL) dried over Na2SO4 collected together and concentrated under reduced pressure to give the title compound in quantitative yield (0.29 g).

Workup

  1. washThe reaction mixture was washed with DCM
  2. additionHCl (1N) was added
  3. extractionextract with DCM (3×10 mL) and AcOEt (3×10 mL)
  4. washThe organic layers were washed with brine (2×10 mL)
  5. dry with materialdried over Na2SO4
  6. customcollected together
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1141768357fb4117a96bbb25ca26f65c
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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