HCID 10028760, compound → HCID 10027612, compound

HRID 1825325Notes

Reaction equation

HRID 1825325 reaction equation
[C:1]([C@H:4]([CH2:31][CH2:32][O:33][CH3:34])[CH2:5][C:6]1([C:11]([NH:13][C@@H:14]([CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH2:15][C:16]([O:18]CC)=[O:17])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1)([OH:3])=[O:2]>O1CCOCC1.[OH-].[Na+]>[C:1]([C@H:4]([CH2:31][CH2:32][O:33][CH3:34])[CH2:5][C:6]1([C:11]([NH:13][C@@H:14]([CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH2:15][C:16]([OH:18])=[O:17])=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10]1)([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 10028760HCID 10028760, compound

Product 1

HCID 10027612HCID 10027612, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of the ester from example 52 (60 mg, 0.12 mmol) in dioxan (4 ml) and 1N sodium hydroxide (4 ml) was stirred at room temperature for 5 hours. The mixture was concentrated under reduced pressure and the residue partitioned between water (20 ml) and ethyl acetate (20 ml). The layers were separated, the aqueous acidified to pH 1 using hydrochloric acid, and this soluton then re-extracted with ethyl acetate (2×20 ml). These combined organic extracts were dried (MgSO4) and evaporated under reduced pressure to afford the title compound, 49 mg; 1H NMR (CDCl3, 400 MHz) δ: 1.42–1.78 (m, 10H), 1.97 (m, 3H), 2.16 (m, 1H), 2.40–2.70 (m, 6H), 3.37 (m, 5H), 3.44 (m, 1H), 4.42 (m, 1H), 6.38 (d, 1H), 7.07 (d, 2H), 7.21 (d, 2H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue partitioned between water (20 ml) and ethyl acetate (20 ml)
  3. customThe layers were separated
  4. extractionthis soluton then re-extracted with ethyl acetate (2×20 ml)
  5. dry with materialThese combined organic extracts were dried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7cb9aa5c496740fc8d2b7d53f5668ee8
Source dataset
uspto-grants-2006_05
Patent number
US07045653B2

Reaction notes

Loading…