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

HRID 716742ノート

反応式

HRID 716742 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-345dbb46db9d4533b8e7e216b550761c
出典データセット
uspto-grants-2015_11
特許番号
US09193669B2

反応ノート

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