1,2-Dichloroethane → Benzyl (S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propanoylamino]-propionate

HRID 751751ノート

反応式

HRID 751751 の反応式
Cl.[CH2:2]([O:9][C:10](=[O:14])[C@H:11]([CH3:13])[NH2:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[C:29]([N:36]([CH3:42])[C@H:37]([C:39](O)=[O:40])[CH3:38])([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].CN1CCOCC1>C1(C)C=CC=CC=1.O.CN(C)C=O>[C:32]([O:31][C:29]([N:36]([CH3:42])[C@@H:37]([CH3:38])[C:39]([NH:12][C@@H:11]([CH3:13])[C:10]([O:9][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:14])=[O:40])=[O:30])([CH3:35])([CH3:34])[CH3:33]

参加物

9

反応物 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 12210893L-Alanine, phenylmethyl ester, hydrochloride (1:1)

生成物 1

HCID 14673102Benzyl (S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propanoylamino]-propionate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

4.81 g (22.3 mmol) of L-alanine benzyl ester hydrochloride, 3.32 g (24.6 mmol) of HOBt and 4.92 g (25.7 mmol) of EDC are introduced into 10 ml of anhydrous dimethylformamide under argon. At 0° C., 4.54 g (22.3 mmol) of N-Boc-N-methyl-L-alanine and 14.7 ml (133.9 mmol) of N-methylmorpholine are added, and the reaction mixture is stirred overnight with slow warming to RT. The reaction solution is treated with water and toluene and extracted with shaking. The aqueous phase is extracted twice with toluene, and the combined organic phases are dried over sodium sulfate and concentrated to dryness after filtration. The product is purified chromatographically by silica gel chromatography on about 1500 ml of silica gel using MeOH/dichloromethane 10/1. 7.9 g (97% of th.) of the product are obtained.

後処理

  1. extractionextracted
  2. stirringwith shaking
  3. extractionThe aqueous phase is extracted twice with toluene
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. filtrationafter filtration
  7. customThe product is purified chromatographically by silica gel chromatography on about 1500 ml of silica gel
  8. custom7.9 g (97% of th.) of the product are obtained

出典と根拠

ORDレコード
ord-7f5857906a5c4b5facf5ffce9d697e85
出典データセット
uspto-grants-2008_07
特許番号
US07405201B2

反応ノート

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