Trityl chloride → H-D-Cys(Trt)-OMe*HCl

HRID 2239031ノート

反応式

HRID 2239031 の反応式
Cl.[CH3:2][O:3][C:4](=[O:9])[C@@H:5]([CH2:7][SH:8])[NH2:6].Cl.C(OCC)(=O)C.[C:17]([Cl:36])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)C>[ClH:36].[CH3:2][O:3][C:4](=[O:9])[C@@H:5]([CH2:7][S:8][C:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[NH2:6]

参加物

7

反応物 4

HCID 6456Trityl chlorideHCID 516892Sodium BicarbonateHCID 637545D-Cysteine Methyl Ester HydrochlorideHCID 21866389Hydrogen chloride-ethyl acetate

生成物 1

HCID 86619907H-D-Cys(Trt)-OMe*HCl収率 64%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

D-Cysteine methyl ester hydrochloride (2.0 g) was suspended in N,N-dimethylformamide (12 mL), 4N hydrochloric acid/ethyl acetate solution (0.5 mL) was added, and the mixture was stirred at room temperature for 20 min. Trityl chloride (3.2 g) was added, and the mixture was stirred at 50° C. for 18 hr, diluted with diethyl ether, and poured into ice water. The mixture was neutralized with saturated aqueous sodium hydrogencarbonate solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (MgSO4), and concentrated. The obtained residue was diluted with ethyl acetate, and 4N hydrochloric acid/ethyl acetate solution (5 mL) was added. The precipitated solid was collected by filtration to give the title compound (3.0 g, yield 64%) as a colorless amorphous solid.

後処理

  1. stirringthe mixture was stirred at 50° C. for 18 hr
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. additionThe obtained residue was diluted with ethyl acetate, and 4N hydrochloric acid/ethyl acetate solution (5 mL)
  7. additionwas added
  8. filtrationThe precipitated solid was collected by filtration

出典と根拠

ORDレコード
ord-243667efd4ae4206976e65c5ed690337
出典データセット
uspto-grants-2010_05
特許番号
US07718798B2

反応ノート

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