Lithium Hydroxide → HCID 178514381, compound

HRID 1069161Notes

Reaction equation

HRID 1069161 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][N:9]=[CH:10][NH:11][C:12]1[CH:13]=[C:14]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([CH:27]([C:36]([NH:38][CH2:39][C:40]([O:42]CC)=[O:41])=[O:37])[CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])=[CH:23][CH:22]=2)=[O:19])[CH:15]=[CH:16][CH:17]=1.C(O)(C(F)(F)F)=O.[OH-].[Li+]>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][N:9]=[CH:10][NH:11][C:12]1[CH:13]=[C:14]([C:18]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([CH:27]([C:36]([NH:38][CH2:39][C:40]([OH:42])=[O:41])=[O:37])[CH2:28][C:29]([OH:31])=[O:30])=[CH:25][CH:26]=2)=[O:19])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 178472789HCID 178472789, compound

Product 1

HCID 178514381HCID 178514381, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

The compound of Example 72 (500 mg) was added to methylene chloride (5 mL) followed by the addition of TFA (2 mL). The reaction was monitored by HPLC. After the reaction was complete the product was freeze dried. The product was added to water/aceonitrile 1:1 (50 mL), followed by the addition of lithium hydroxide (100 mg, 0.4 mmol). The reaction was stirred at 25° C., and monitored by HPLC. After complete hydrolysis the product was extracted with ethyl acetate and dried over Na2SO4 to give a yellow oil (450 mg). NMR and MS were consistent with the proposed structure.

Workup

  1. customdried
  2. additionThe product was added to water/
  3. customAfter complete hydrolysis the product
  4. extractionwas extracted with ethyl acetate
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-b702e48375224a209bd6f8d6d76f6167
Source dataset
uspto-grants-2001_06
Patent number
US06251944B1

Reaction notes

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