Potassium Carbonate → {N-[(1R)-1-Carbamoyl-3-methyl-butyl]-N-(4-chlorobenzenesulfonyl)amino}acetic acid tert-butyl ester

HRID 507303ノート

反応式

HRID 507303 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([NH2:15])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:26]([O:30][C:31](=[O:34])[CH2:32]Br)([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C>[C:26]([O:30][C:31](=[O:34])[CH2:32][N:11]([C@@H:12]([C:13](=[O:14])[NH2:15])[CH2:16][CH:17]([CH3:19])[CH3:18])[S:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)(=[O:9])=[O:10])([CH3:29])([CH3:28])[CH3:27]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 59001058(2R)-2-(4-Chlorobenzenesulfonylamino)-4-methylpentanoic acid amide

生成物 1

HCID 59001051{N-[(1R)-1-Carbamoyl-3-methyl-butyl]-N-(4-chlorobenzenesulfonyl)amino}acetic acid tert-butyl ester収率 35%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

(2R)-2-(4-Chlorobenzenesulfonylamino)-4-methylpentanoic acid amide (3.00 g, 9.87 mmol) was dissolved in DMF (50 mL). To the solution was added potassium carbonate (6.0 g, 39 mmol) and bromoacetic acid tert-butyl ester (6.0 mL, 39 mmol). The solution was heated to 70° C. for 3 h. The reaction was quenched with EtOAc and saturated NaHCO3. The organic layer was washed with brine, dried over MgSO4, and concentrated. The crude oil was further purified on a Biotage 40M (loaded in CH2Cl2, eluted in 30% EtOAc/hexanes) to afford a white powder (1.2 g, 35%). MS (ESI), (M+H)+ 446.3; 1H NMR (CDCl3) δ 7.76 (d, 2H, J=8.0), 7.52 (d, 2H, J=8.0), 6.61 (br s, 1H) 5.45 (s, 1H), 4.15-4.18 (m, 1H), 3.09-3.24 (m, 2H), 2.50-2.58 (m, 4H), 2.31-2.39 (m, 2H), 1.92-1.99 (m, 1H), 1.15-1.59 (m, 8H), 1.00-1.04 (m, 7H), 0.71-0.74 (m, 6H).

後処理

  1. customThe reaction was quenched with EtOAc and saturated NaHCO3
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude oil was further purified on a Biotage 40M (loaded in CH2Cl2, eluted in 30% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-a6e288e44f13429880b7f1f2eadaef70
出典データセット
uspto-grants-2010_08
特許番号
US07786122B2

反応ノート

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