Hydrochloric Acid → Ethyl-7-{[4-(1-Hydroxy-3-phenyl-propyl)-benzyl]-methanesulfonyl-amino}-heptanoate

HRID 1698989Notes

Reaction equation

HRID 1698989 reaction equation
[CH:1]([C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]([S:20]([CH3:23])(=[O:22])=[O:21])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][CH:4]=1)=[O:2].[CH2:26]([Mg]Cl)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O.Cl>C(Cl)Cl>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:8]([CH2:7][C:6]1[CH:5]=[CH:4][C:3]([CH:1]([OH:2])[CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:25][CH:24]=1)[S:20]([CH3:23])(=[O:22])=[O:21])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 22246810Ethyl 7-[(4-formyl-benzyl)-methanesulfonyl-amino]-heptanoateHCID 178418865HCID 178418865, compound

Product 1

HCID 22246896Ethyl-7-{[4-(1-Hydroxy-3-phenyl-propyl)-benzyl]-methanesulfonyl-amino}-heptanoateYield 15.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 7-[(4-formyl-benzyl)-methanesulfonyl-amino]-heptanoate (200 mg, 0.54 mmol) in CH2Cl2 (2.5 mL) was cooled to 0° C. Phenethylmagnesium chloride (0.6 mL, 1M in THF, 0.6 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 24 h. Water and HCl (1N) were added and the aqueous solution was extracted with CH2Cl2. The organic solution was washed with water (1×) followed by brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. The product was purified by flash chromatography (10% EtOAc/hex to 40% EtOAc/hex) to afford the title compound of Step A (40 mg). 1H NMR (400 MHz, CDCl3) δ7.95 (d, 1H), 7.45 (d, 1H), 7.13-7.40 (m, 7H), 4.65-4.73 (m, 1H), 4.324.46 (m, 2H), 4.11 (q, 2H), 3.25-3.35 (m, 1H), 3.00-3.22 (m, 2H), 2.83 (s, 3H), 2.60-2.81 (m, 1H), 1.96-2.34 (m, 4H), 1.15-1.70 (m, 12H); MS 493 (M+18).

Workup

  1. extractionthe aqueous solution was extracted with CH2Cl2
  2. washThe organic solution was washed with water (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography (10% EtOAc/hex to 40% EtOAc/hex)

Sources & evidence

ORD record
ord-754761ab067e416583f326895898b058
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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