Diethyl Pyrocarbonate → HCID 178454220、化合物

HRID 539510

反応式

HRID 539510 の反応式
[NH:1]([C:13]([O:15]CC1C=CC=CC=1)=O)[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:23]1[CH:27]=[N:26][N:25]=[N:24]1.[NH:28]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C@H:29](C(O)=O)[CH2:30][NH2:31].CCOC(OC(OCC)=O)=O.CCN(C(C)C)C(C)C>C(O)C.[Pd]>[NH:28]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C@H:29]([C:13]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:15])[CH2:30][NH2:31].[NH:23]1[CH:27]=[N:26][N:25]=[N:24]1

参加物

7

反応物 4

HCID 3051Diethyl PyrocarbonateHCID 81531DiisopropylethylamineHCID 2755946Boc-Dap-OHHCID 178523858HCID 178523858、化合物

生成物 1

HCID 178454220HCID 178454220、化合物収率 26.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

Cbz-Phe-Tetrazole (2.25 g, 6.25 mmole) was then dissolved in ethanol (100 ml) and treated with Pd/C 10% (500 mg, 0.3125 mmole) and stirred under hydrogen for 2 hr. The reaction mixture was filtered through a celite pad and concentrated to dryness. This material was reconstituted in dichloromethane (80 ml) and treated with Boc-Dap (1.88 g, 6.54 mmole), DEPC (1.42 ml, 9.38 mmole) and DIEA (3.8 ml, 21.88 mmole). After 16 hr volatiles were removed to afford crude Boc-Dap-Phe-Tetrazole which was purified by preparative HPLC to give 704 mg (20%) of 1001 as a white powder. Reverse-phase HPLC analysis: 99% at 6.3 min; LCMS (ESI): m/z 458.905 (MH)+, 480.874 (M+Na)+, eluted at 12.95 min.

後処理

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationconcentrated to dryness
  3. customAfter 16 hr volatiles were removed
  4. customto afford crude Boc-Dap-Phe-Tetrazole which
  5. customwas purified by preparative HPLC

出典と根拠

ORDレコード
ord-7892f38f1d72443b83d61b050e7f587c
出典データセット
uspto-grants-2014_10
特許番号
US08871720B2

関連ノート

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