Lithium Hydroxide → HCID 68409585, compound

HRID 1443435Notes

Reaction equation

HRID 1443435 reaction equation
C([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=[C:22]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:21]=3)[CH2:16][CH:15]2[C:36](=[O:45])[N:37]([CH2:39][CH2:40][CH2:41][CH2:42][CH:43]=[CH2:44])[CH3:38])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])C.[Li+].[OH-]>CN(C=O)C>[CH2:39]([N:37]([CH3:38])[C:36]([CH:15]1[CH2:16][CH:17]([O:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:21]=2)[CH2:18][CH:14]1[C:12]([NH:11][C:6]1([C:4]([OH:5])=[O:3])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:13])=[O:45])[CH2:40][CH2:41][CH2:42][CH:43]=[CH2:44]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68411373HCID 68411373, compound

Product 1

HCID 68409585HCID 68409585, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Compound 28 (0.17 g, 0.27 mmol) was dissolved in DMF (2.5 mL) and transferred to a microwave vial. LiOH (aq, 2 M, 8 mL) was added and the reaction was heated in the microwave at 130° C. for 1 h. Quenched the reaction with HCl (aq, 1M) to pH 1 and extracted with DCM (3×20 mL). Combined organic phases were washed with HCl (aq, 1M, 20 mL) and H2O (3×30 mL). Water phase was back-extracted with DCM (2×30 mL). Organic phases were dried over MgSO4, filtered and evaporated. Purified by flash chromatography (DCM/MeOH) to yield the title compound (0.08 g, 49%).

Workup

  1. customQuenched
  2. customthe reaction with HCl (aq, 1M) to pH 1
  3. extractionextracted with DCM (3×20 mL)
  4. washCombined organic phases were washed with HCl (aq, 1M, 20 mL) and H2O (3×30 mL)
  5. extractionWater phase was back-extracted with DCM (2×30 mL)
  6. dry with materialOrganic phases were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customPurified by flash chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-595aff8dbafc46a582a2cd9334ad7ea8
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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