Hydrochloric Acid → HCID 22246896, compound

HRID 480271Notes

Reaction equation

HRID 480271 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 22246810HCID 22246810, compoundHCID 178418865HCID 178418865, compound

Product 1

HCID 22246896HCID 22246896, compoundYield 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) δ 6 7.95 (d, 1H), 7.45 (d, 1H), 7.13-7.40 (m, 7H), 4.654.73 (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-813ab8dee6fd4027972382315620c122
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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