Pentane-2-sulfonyl chloride → Tert-butyl 2-(3-(1-methylbutylsulfonamido)phenoxy)ethylcarbamate

HRID 1189923Notes

Reaction equation

HRID 1189923 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[CH3:19][CH:20]([S:24](Cl)(=[O:26])=[O:25])[CH2:21][CH2:22][CH3:23]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:19][CH:20]([S:24]([NH:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:26])=[O:25])[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 2760314Pentane-2-sulfonyl chlorideHCID 11557882tert-butyl N-[2-(3-aminophenoxy)ethyl]carbamate

Product 1

HCID 59316954Tert-butyl 2-(3-(1-methylbutylsulfonamido)phenoxy)ethylcarbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of tert-butyl 2-(3-aminophenoxy)ethylcarbamate (3) (210 mg, 1.1 mmol), 2-pentylsulfonyl chloride (4) (0.17 ml, 1.1 mmol) and DMAP (20 mg) in pyridine (5 ml) was stirred at room temperature under argon for 15 hours. The solvent was evaporated under reduced pressure. The residue was partitioned between EtOAc and 0.5 N HCl aq. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (40 to 60% EtOAc-hexanes gradient) gave tert-butyl 2-(3-(1-methylbutylsulfonamido)phenoxy)ethylcarbamate (5) as light yellow oil. Yield (160 mg, 46%). 1H NMR (400 MHz, CDCl3) δ 7.20 (t, J=8.0 Hz, 1H), 6.75-6.82 (m, 1H), 6.73-6.75 (m, 1H), 6.64-6.67 (m, 1H), 6.37 (bs, 1H), 4.96 (bs, 1H), 3.99 (t, J=6.0 Hz, 2H), 3.51 (q, J=6.0 Hz, 2H), 3.11-3.18 (m, 1H), 1.91-2.0 (m, 1H), 1.53-1.60 (m, 2H), 1.44 (s, 9H), 1.23-1.37 (m, 4H), 0.88-0.91 (m, 3H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was partitioned between EtOAc and 0.5 N HCl aq. The organic layer
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography (40 to 60% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-904188008d3e48ec926cc73e959adab8
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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