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Formic Acid → N-(tert-Butoxycarbonyl)-O-{[(3S)-3-[(tert-butoxycarbonyl)amino]-4-oxo-4-{[2-(tritylsulfanyl)-ethyl]amino}butyl]carbamoyl}-L-tyrosine

HRID 630678
ノート
印刷プレビュー

反応式

HRID 630678 の反応式
C([O:4][C:5](=[O:62])[C@H:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23](=[O:61])[NH:24][CH2:25][CH2:26][C@H:27]([NH:53][C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[C:28](=[O:52])[NH:29][CH2:30][CH2:31][S:32][C:33]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:18][CH:17]=1)[NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])C=C.C(N(CC)CC)C.C(O)=O>O1CCCC1.O>[C:11]([O:10][C:8]([NH:7][C@H:6]([C:5]([OH:62])=[O:4])[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][C:23](=[O:61])[NH:24][CH2:25][CH2:26][C@H:27]([NH:53][C:54]([O:56][C:57]([CH3:59])([CH3:58])[CH3:60])=[O:55])[C:28](=[O:52])[NH:29][CH2:30][CH2:31][S:32][C:33]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[CH:20][CH:21]=1)=[O:9])([CH3:12])([CH3:13])[CH3:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 117893244Allyl-N-(tert-butoxycarbonyl)-O-{[(3S)-3-[(tert-butoxycarbonyl)amino]-4-oxo-4-{[2-(tritylsulfanyl)ethyl]amino}butyl]carbamoyl}-L-tyrosinate

生成物 1

HCID 71557574N-(tert-Butoxycarbonyl)-O-{[(3S)-3-[(tert-butoxycarbonyl)amino]-4-oxo-4-{[2-(tritylsulfanyl)-ethyl]amino}butyl]carbamoyl}-L-tyrosine

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

98 mg (0.1 mmol) of the compound from example 15A was dissolved in approx. 4 ml tetrahydrofuran. 70 μl (0.5 mmol) Triethylamine, 19 μl (0.5 mmol) formic acid and 11 mg (0.01 mmol) tetrakis(triphenylphosphin)palladium(0) were added. The reaction mixture was stirred over night at room temperature. The reaction was diluted with approx. 5 ml water and twice extracted with approx. 5 ml dichloromethane. The combined organic phases were extracted with brine, dried over sodium sulfate and concentrated to dryness under reduced pressure. The raw product was purified by preparative RP-HPLC on a C18 column with a water/methanol gradient to yield 67 mg (79% of theory) product.

後処理

  1. extractiontwice extracted with approx. 5 ml dichloromethane
  2. extractionThe combined organic phases were extracted with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe raw product was purified by preparative RP-HPLC on a C18 column with a water/methanol gradient
  6. customto yield 67 mg (79% of theory) product

出典と根拠

ORDレコード
ord-7452d2bea8304b4488fdc607a81c73c0
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09315543B2

反応ノート

読み込み中…

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