Hydrochloric Acid → HCID 140536906, compound

HRID 1667607Notes

Reaction equation

HRID 1667607 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([C:14]1[CH:38]=[CH:37][C:17]([O:18][CH:19]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH:31]([CH3:33])[CH3:32])=[C:26]([O:34][CH2:35][CH3:36])[CH:25]=2)[C:20]([O:22]C)=[O:21])=[CH:16][CH:15]=1)=[NH:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].Cl>C1COCC1.CO>[CH2:1]([O:8][C:9]([NH:11][C:12]([C:14]1[CH:38]=[CH:37][C:17]([O:18][CH:19]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH:31]([CH3:32])[CH3:33])=[C:26]([O:34][CH2:35][CH3:36])[CH:25]=2)[C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1)=[NH:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 140536904HCID 140536904, compound

Product 1

HCID 140536906HCID 140536906, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 9D (570 mg, 1.09 mmol) in THF (6.0 mL) and MeOH (0.5 mL) was added LiOH (1.0 M, 1.92 mL, 1.92 mmol). The mixture was stirred at rt for 1.0 h before it was acidified with 1.0 N HCl (5.0 mL). The mixture was extracted with ethyl acetate, washed with brine and dried over Na2SO4. After removal of solvent, 9E (500 mg, 90% yield) was obtained as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (d, J=6.16 Hz, 6H) 1.30 (t, J=7.03 Hz, 3H) 4.00 (q, J=7.03 Hz, 2H) 4.49 (m, 1H) 5.09 (s, 2H) 5.85 (s, 1H) 6.90-7.38 (m, 11H) 7.95 (d, J=9.20 Hz, 2H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter removal of solvent

Sources & evidence

ORD record
ord-ea73df253a4843fcb6ec7c875adf0751
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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