Lithium Hydroxide → HCID 57936081, compound

HRID 1672544Notes

Reaction equation

HRID 1672544 reaction equation
CO[C@H](C1C=CC=CC=1)C([O:6][C@H:7]1[CH2:16][CH2:15][C:14]2[C:9](=[C:10]([NH2:17])[CH:11]=[CH:12][CH:13]=2)[CH2:8]1)=O.[OH-].[Li+].C([O-])(O)=O.[Na+]>O1CCCC1.C(OCC)(=O)C>[NH2:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH2:8][C@@H:7]([OH:6])[CH2:16][CH2:15]2

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 516892Sodium BicarbonateHCID 91020827HCID 91020827, compound

Product 1

HCID 57936081HCID 57936081, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 25A (300 mg, 0.963 mmol) in tetrahydrofuran (4 mL) and aqueous lithium hydroxide (1 M aq, 3 mL, 3.00 mmol) was stirred at ambient temperature for 1.5 hour. The reaction was diluted with ethyl acetate and poured into aqueous saturated NaHCO3 solution. The separated organic phase was washed with brine, dried over Na2SO4, and concentrated in vacuo. The result was 145 mg (92% yield) of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 6.76 (t, 1H), 6.41 (d, 1H), 6.28 (d, 1H), 4.74, (d, 1H), 4.66 (bs, 2H), 3.90 (m, 1H), 2.52-2.79 (m, 3H), 2.17 (m, 1H), 1.83 (m, 1H), 1.55 (m, 1H). MS (DCI+) m/z 164 (M+H)+, 181 (M+NH4)+.

Workup

  1. washThe separated organic phase was washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7faef17084c140c6a84902943ff0fcfe
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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