Lithium Hydroxide → HCID 11415622, compound

HRID 229736Notes

Reaction equation

HRID 229736 reaction equation
[OH:1][C@@:2]12[C:20](=[O:21])[O:19][C@@H:4]([C@H:5]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=3)[CH:6]=[CH:7]1)[CH2:3]2.[OH-:22].[Li+]>C1COCC1.O>[OH:1][C@@:2]1([C:20]([OH:19])=[O:21])[CH:7]=[CH:6][C@@H:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[C@H:4]([OH:22])[CH2:3]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 11369807HCID 11369807, compound

Product 1

HCID 11415622HCID 11415622, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of carbolactone VIII (28 mg, 0.10 mmol) in 1 mL of THF and 0.5 mL of a 0.5 M lithium hydroxide aqueous solution was stirred at room temperature for 1 hour. The resulting solution was diluted with milliQ water (5 mL) and treated with Amberlite IR-120 (H+) to pH 6. The resin was filtered and washed with milliQ water (15 mL). The filtrate was concentrated under reduced pressure to give 23 mg of acid IX (74%) in a pale solid yellow form. [α]25D−121° (c 1.1 in CH3OH); 1H-NMR (250 MHz, CD3OD, δ) 8.20 (d, 2H, J 8.8), 7.65 (d, 2H, J 8.8), 5.93 (dd, 1H, J 10.0 and 1.8), 5.73 (d, 1H, J 10.0), 4.84 (s, 2H), 4.04 (m, 1H), 3.93 (dt, 1H, J 7.9 and 1.8) and 2.07 (m, 2H); 13C-NMR (63 MHz, CD3OD, δ) 176.8, 147.6, 147.1, 130.4, 129.3, 128.1, 123.4, 81.1, 73.5, 70.4, 68.2 and 40.2; IR (KBr)/cm−1 3528 and 1596; EM-IQ+ (m/z) 310 (MH+); HRMS calculated for C14H16NO7 (MH+): 310.0928, 310.0928 found.

Workup

  1. additiontreated with Amberlite IR-120 (H+) to pH 6
  2. filtrationThe resin was filtered
  3. washwashed with milliQ water (15 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e74c186637f64d42a4b8a1290ad91738
Source dataset
uspto-grants-2009_07
Patent number
US07563896B2

Reaction notes

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