Potassium Carbonate → HCID 54128034、化合物

HRID 1594533ノート

反応式

HRID 1594533 の反応式
[C:1]([O:5][C:6](=[O:29])[C@@H:7]([CH:26]([CH3:28])[CH3:27])[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[N:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH2:43]Cl)[CH:38]=1.Cl.N1C=CC=CC=1CCl>CN(C=O)C.C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:29])[C@@H:7]([CH:26]([CH3:27])[CH3:28])[N:8]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:20]=[CH:21][C:22]([Br:25])=[CH:23][CH:24]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[CH2:43][C:39]1[CH:38]=[N:37][CH:42]=[CH:41][CH:40]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 54527823HCID 54527823、化合物

生成物 1

HCID 54128034HCID 54128034、化合物収率 92%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-[4-(4-bromophenoxy)benzenesulfonyl]-D-valine t-butyl ester (980 mg, 2.0 mol) in 5 mL of DMF was added potassium carbonate (1.53 g, 11.1 mol), 3-picolyl chloride hydrochloride (414 mg, 2.53 mol), and Kl (67 mg, 0.4 mol). The reaction was stirred at room temperature overnight. An additional 220 mg of picolyl chloride hydrochloride was added, and the reaction was stirred for 3 h. Water (25 mL) and ethyl acetate (50 mL) were added, and the layers were separated. The ethyl acetate fraction was washed with brine, dried over MgSO4, and concentrated. The residue was purified by chromatography on silica, eluting with 35% ethyl acetate in hexane, to give 1.07g (92%) of N-[4-(4-bromophenoxy)benzenesulfonyl]-N-(pyridin-3-yl)methyl-D-valine t-butyl ester as a tan foam.

後処理

  1. stirringthe reaction was stirred for 3 h
  2. customthe layers were separated
  3. washThe ethyl acetate fraction was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica
  7. washeluting with 35% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-fef0d59174374a2192cf50dc698d949c
出典データセット
uspto-grants-2001_09
特許番号
USH0001992H1

反応ノート

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