Lithium Hydroxide → HCID 57609740, compound

HRID 416672Notes

Reaction equation

HRID 416672 reaction equation
C[O:2][C:3](=[O:36])[CH:4]([N:6]([C:16](=[O:35])[CH:17]([CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C:18](=[O:27])[CH2:19][CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH3:5].[Li+].[OH-]>C1COCC1.O>[CH:21]1([CH2:20][CH2:19][C:18](=[O:27])[CH:17]([CH2:28][CH:29]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]2)[C:16]([N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH:4]([CH3:5])[C:3]([OH:36])=[O:2])=[O:35])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57609698HCID 57609698, compound

Product 1

HCID 57609740HCID 57609740, compoundYield 80%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of methyl esters 59 (200 mg, 4.00 mmol) in THF/H2O (25 mL/4.5 mL) was added LiOH (1 M in H2O, 0.50 mL, 4.4 mmol) at 10° C. dropwise. The reaction mixture was stirred at ambient temperature for 12 h and THF was removed under reduced pressure. The aqueous layer was acidified to pH2 with 1 M HCl and extracted with CH2Cl2 (25 mL×3). The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (1:3 EtOAc/hexanes) to give the desired acids 60 (155 mg, 80%) as a white solid. IR (neat) 3199, 1719, 1648, 1612 cm−1; 1H NMR (500 MHz, CDCl3) δ 7.18 (d, J=8.5 Hz, 2H), 6.89 (d, J=9.0 Hz, 2H), 4.69 (d, J=17.5 Hz, 1H), 4.54 (q, J=7.0 Hz, 1H), 4.34 (d, J=17.0 Hz, 1H), 3.80 (s, 3H), 3.64 (dd, J=5.5, 8.5 Hz, 2H), 2.49 (dd, J=7.0, 8.5 Hz, 2H), 1.91 (ddd, J=6.0, 8.5, 14.0 Hz, 1H), 0.69-1.70 (m, 28H); LRMS (ESI) Calcd. for C29H43NO5 [M+H] 486, found 486.

Workup

  1. customTHF was removed under reduced pressure
  2. extractionextracted with CH2Cl2 (25 mL×3)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (1:3 EtOAc/hexanes)

Sources & evidence

ORD record
ord-e9edb1d92ca248f3a5bad04feb1f6d89
Source dataset
uspto-grants-2012_01
Patent number
US08088923B2

Reaction notes

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