Lithium hydroxide, monohydrate → HCID 11364780, compound

HRID 735842Notes

Reaction equation

HRID 735842 reaction equation
C([O:3][C:4](=[O:42])[C:5]([N:7]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:28])=[CH:23][CH:22]=1)[CH:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[CH3:9])=[O:6])C.O.[OH-].[Li+]>C1COCC1.O>[CH2:30]([NH:29][C:27]([C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:7]([C:5](=[O:6])[C:4]([OH:42])=[O:3])[CH:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[CH3:9])=[CH:26][CH:25]=1)=[O:28])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67187691HCID 67187691, compound

Product 1

HCID 11364780HCID 11364780, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The resin-bound ethyl{{4-[(dodecylamino)carbonyl]benzyl}[1-(1-naphthyl)ethyl]amino}-(oxo)acetate (described in step d, 0.0426 mmol) was swelled in THF (0.300 mL) for 15 min at rt. Lithium hydroxide monohydrate (36 mg, 0.852 mmol) diluted in H2O (0.060 mL) was added and the resulting reaction mixture was shaken 14 h at rt. The resin was washed successively with THF (1×15 min), H2O (1×15 min), MeOH (1×15 min), THF (1×15 min), MeOH (3×10 min), DMF (3×10 min), MeOH (1×5 min), THF (3×10 min), MeOH (1×5 min), DCM (3×10 min) and with Et2O (1×10 min). The resin was then dried under vacuum to afford the resin-bound {{4-[(dodecylamino)carbonyl]benzyl}[1-(1-naphthyl)-ethyl]amino}(oxo)acetic acid which was used directly in the next step.

Workup

  1. additionwas added
  2. customthe resulting reaction mixture
  3. washThe resin was washed successively with THF (1×15 min), H2O (1×15 min), MeOH (1×15 min), THF (1×15 min), MeOH (3×10 min), DMF (3×10 min), MeOH (1×5 min), THF (3×10 min), MeOH (1×5 min), DCM (3×10 min) and with Et2O (1×10 min)
  4. customThe resin was then dried under vacuum

Sources & evidence

ORD record
ord-700b70ad4b8247df8936669601afc823
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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