Lithium hydroxide, monohydrate → HCID 68632114, compound

HRID 1160144Notes

Reaction equation

HRID 1160144 reaction equation
C[O:2][C:3]([CH:5]1[N:10]([C:11](=[O:34])[CH:12]([NH:17][C:18]([NH:20][C:21]2([CH2:27][S:28](=[O:33])(=[O:32])[N:29]([CH3:31])[CH3:30])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:19])[C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:9][CH:8]2[CH:6]1[C:7]2([CH3:36])[CH3:35])=[O:4].O.[OH-].[Li+]>C1COCC1.O>[CH3:31][N:29]([CH3:30])[S:28]([CH2:27][C:21]1([NH:20][C:18](=[O:19])[NH:17][CH:12]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]([N:10]2[CH2:9][CH:8]3[CH:6]([C:7]3([CH3:36])[CH3:35])[CH:5]2[C:3]([OH:4])=[O:2])=[O:34])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)(=[O:33])=[O:32]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68630836HCID 68630836, compound

Product 1

HCID 68632114HCID 68632114, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

A solution of methylester 1200-F (840 mg) in 30 mL of a 2:1 mixture of THF/water was cooled to 0° C. and treated with lithium hydroxide monohydrate (2.5 eq, 166 mg). The mixture was stirred for 10 min and the cooling bath was removed. The reaction was stirred at room temp until all starting material had been consumed as determined by TLC (acetone/hexanes; 3:7). After 2 h, the mixture was treated with aqueous 1M HCl (aprox 50 mL) turning the mixture acidic (pH 2). The mixture was extracted with dichloromethane (3×50 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the product 1200-G (815 mg-98%) as a white solid.

Workup

  1. customthe cooling bath was removed
  2. stirringThe reaction was stirred at room temp until all starting material
  3. customhad been consumed
  4. waitAfter 2 h
  5. additionthe mixture was treated with aqueous 1M HCl (aprox 50 mL)
  6. extractionThe mixture was extracted with dichloromethane (3×50 mL)
  7. dry with materialThe combined organic layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8f3c8677e1fd4cdfbc40ca2fc4911b3c
Source dataset
uspto-grants-2010_10
Patent number
US07816326B2

Reaction notes

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