Ammonium Chloride → 4-{2-[(r)-2-((e)-3-Hydroxy-3-pentyl-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-ethylsulfanyl}-butyric acid

HRID 22976Notes

Reaction equation

HRID 22976 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C@H:4](/[CH:7]=[CH:8]/[C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[N:3]1[CH2:16][CH2:17][S:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]C)=[O:23].[CH2:26]([Mg]Br)[CH2:27][CH2:28][CH2:29][CH3:30].[Cl-].[NH4+]>O1CCCC1>[OH:15][C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])/[CH:8]=[CH:7]/[C@H:4]1[CH2:5][CH2:6][C:2](=[O:1])[N:3]1[CH2:16][CH2:17][S:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 12132851methyl 4-[(2-{(5R)-2-oxo-5-[(1E)-3-oxooct-1-enyl] pyrrolidin-1-yl}ethyl)thio]-butanoateHCID 178445865HCID 178445865, compound

Product 1

HCID 101809364-{2-[(r)-2-((e)-3-Hydroxy-3-pentyl-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-ethylsulfanyl}-butyric acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −24° C. tetrahydrofuran (38 mL) solution of enone (from Example 1, step 3, 1.52 g) was treated with n-pentylmagnesium bromide (1.8 mL, 2 M ether solution from Aldrich). After 1 hour, the mixture was poured into aqueous ammonium chloride and extracted with ethyl acetate. Following drying and filtration, the desired alcohol (780 mg) was obtained after silica gel chromatography (elute with 5% methanol in ethyl acetate).

Workup

  1. extractionextracted with ethyl acetate
  2. customFollowing drying
  3. filtrationfiltration

Sources & evidence

ORD record
ord-bc2af9341eda4441b8a56f31dd81762c
Source dataset
uspto-grants-2005_02
Patent number
US06849657B2

Reaction notes

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