Triethylamine → HCID 57937825, compound

HRID 1435078Notes

Reaction equation

HRID 1435078 reaction equation
[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)=[C:16]([CH3:27])[CH:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl>[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][S:37]([CH3:36])(=[O:39])=[O:38])=[CH:22][CH:21]=2)=[C:16]([CH3:27])[CH:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57937838HCID 57937838, compound

Product 1

HCID 57937825HCID 57937825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

(4′-Amino-2-methyl-biphenyl-4-ylmethyl)-(3-methyl-butyl)-carbamic acid tert-butyl ester, (I-9b: 128 mg, 0.335 mmol) was dissolved in 7 ml of dichloromethane and treated with triethylamine (0.188 mL, 1.34 mmol) and methylsulfonyl chloride (0.077 mL, 1.0 mmol). After 12 hours, the volatiles were removed under reduced pressure and the residue was then dissolved in methanol (15 mL) and treated with a 2N sodium hydroxide solution (15 mL). After stirring at 50° C. for 1 hour, the reaction mixture was then concentrated under reduced pressure and residue dissolved in ethyl acetate and extracted with water. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified using preparative thin layer chromatography eluting with 65% ethyl acetate in heptane to afford the title compound (I-8c).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. dissolutionthe residue was then dissolved in methanol (15 mL)
  3. additiontreated with a 2N sodium hydroxide solution (15 mL)
  4. concentrationthe reaction mixture was then concentrated under reduced pressure and residue
  5. dissolutiondissolved in ethyl acetate
  6. extractionextracted with water
  7. washThe organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified
  12. washeluting with 65% ethyl acetate in heptane

Sources & evidence

ORD record
ord-828e5388797e4732aea2f2a421b0a5ed
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

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