Hydrochloric Acid → HCID 69601053, compound

HRID 2215086Notes

Reaction equation

HRID 2215086 reaction equation
[OH:1][CH:2]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][S:8][C:7](=[O:10])[N:6]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=[O:18].C1COCC1.[OH-].[Li+].Cl>O.CO>[OH:1][CH:2]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][S:8][C:7](=[O:10])[N:6]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69600997HCID 69600997, compound

Product 1

HCID 69601053HCID 69601053, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3-8 (45 mg, 0.11 mmol) in 5.5 mL 2:2:1 THF:MeOH:water, at 0° C., was added lithium hydroxide (170 μL of a 2M solution in water) and the resulting solution was allowed to warm up to room temperature and stirred overnight. To the solution was added a 1M aqueous solution of HCl (1 mL) and the solution was extracted with ethyl acetate. The organic phases were then combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The compound was purified by flash chromatography using 50–100% ethyl acetate/hexanes to yield 37 mg of 3-9 as a white solid. 1H NMR (400 MHz, CD3OD): δ 7.30–7.18 (m, 5H), 5.81 (dd, 1H), 5.53 (dd, 1H), 4.39 (q, 1H), 4.33 (q, 1H), 3.45 (dd, 1H), 3.33 (m, 1H), 2.97 (m, 2H), 2.77 (dd, 1H), 2.67 (m, 1H), 2.30 (t, 2H), 1.65–1.21 (m, 8H); MS (+ESI): m/z 378.2 (M+1)+.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-8ed57bee401a495fb629a5d797ba7515
Source dataset
uspto-grants-2006_09
Patent number
US07109223B2

Reaction notes

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