Lithium hydroxide, monohydrate → HCID 22402465, compound

HRID 260127Notes

Reaction equation

HRID 260127 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH:19]2[CH2:27][C:26]3[C:21](=[CH:22][C:23]([C:28]([O:30]C)=[O:29])=[CH:24][CH:25]=3)[C:20]2=[O:32])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.CO.O.O[Li].O>CCOC(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18][CH:19]2[CH2:27][C:26]3[C:21](=[CH:22][C:23]([C:28]([OH:30])=[O:29])=[CH:24][CH:25]=3)[C:20]2=[O:32])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21892291Methanol tetrahydrofuran waterHCID 22402466HCID 22402466, compound

Product 1

HCID 22402465HCID 22402465, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-3 (0.6 g, 1.6 mmol) in 1:1:1 THF/CH3OH/H2O (12 mL) was treated with LiOH·H2O (0.34 g, 8 mmol) at room temperature for 2 h. The solution was diluted with EtOAc and extracted with saturated NaHCO3 solution. The basic aqueous layer was acidified to pH 3-4 with 10% KHSO4 solution and extracted with EtOAc. The organic layers were dried (MgSO4), filtered, and evaporated to give 1-4 as a brown oil. Rf (9:0.5:0.5 CH2Cl2 /CH3OH/HOAc) 0.36 1H NMR (300 MHz, CD3OD) δ 8.28 (m, 2H), 7.7 (d, 1H), 7.3 (m, 5H), 5.1 (s, 2H), 4.12 (d, 2H), 3.45 (m, 1H), 2.9 (dd, 1H), 2.8 (m, 2H), 2.4 (dd, 1H), 1.7 (bd, 2H), 1.6-1.0 (m, 7H).

Workup

  1. extractionextracted with saturated NaHCO3 solution
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f03fadb386f14442898750f58bd062c2
Source dataset
uspto-grants-1996_06
Patent number
US05525617

Reaction notes

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