Hydrochloric Acid → HCID 11624910, compound

HRID 2223788Notes

Reaction equation

HRID 2223788 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][CH:7]([CH3:26])[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:13][CH:12]=1.C(N(CC)CC)C.Cl>ClCCl>[CH3:6][CH:7]([CH3:26])[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11659339HCID 11659339, compound2×

Product 1

HCID 11624910HCID 11624910, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonylchloride (93 mg, 63 μL, 0.82 mmol) was added in one portion to a stirred solution of 1,1-dimethylethyl N-{4-[(3-methylbutyl)oxy]phenyl}glycinate (intermediate 6, 0.20 g, 0.68 mmol) and triethylamine (138 mg, 189 μL, 1.36 mmol) in dichloromethane (2 mL) at room temperature under a nitrogen atmosphere. Stirring was continued for 3 h then aqueous hydrochloric acid (1.0 M; 2 mL) was added. The organic phase was separated and the aqueous phase washed with dichloromethane (3×5 mL). The organic phases were combined, dried (magnesium sulfate) then evaporated to dryness. The residue was chromatographed on silica gel (30% diethyl ether:cyclohexane) to give the title compound as a white solid (140 mg, 56%). LC/MS: 3.72 min; z/e 389, calcd (M+18) 389. 1H NMR (400 MHz; CDCl3): 0.95 (6H), 1.45 (9H), 1.70 (2H), 1.85 (1H), 3.10 (3H), 3.95 (2H), 4.30 (2H), 6.85 (2H), 7.35 (2H).

Workup

  1. customThe organic phase was separated
  2. washthe aqueous phase washed with dichloromethane (3×5 mL)
  3. dry with materialdried (magnesium sulfate)
  4. customthen evaporated to dryness
  5. customThe residue was chromatographed on silica gel (30% diethyl ether:cyclohexane)

Sources & evidence

ORD record
ord-fe25a57412224092906c5aeeb5faad8e
Source dataset
uspto-grants-2008_05
Patent number
US07375248B2

Reaction notes

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