Formic Acid → N-[(2S)-2-[(tert-Butoxycarbonyl)amino]-4-{[(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-2-carboxyethyl}phenoxy)carbonyl]amino}butanoyl]-S-trityl-L-cysteinylglycinamide

HRID 630679ノート

反応式

HRID 630679 の反応式
C([O:4][C:5](=[O:69])[C@@H:6]([NH:61][C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:7][C:8]1[CH:60]=[CH:59][C:11]([O:12][C:13]([NH:15][CH2:16][CH2:17][C@H:18]([NH:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C:19]([NH:21][C@H:22]([C:44]([NH:46][CH2:47][C:48]([NH2:50])=[O:49])=[O:45])[CH2:23][S:24][C:25]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:20])=[O:14])=[CH:10][CH:9]=1)C=C.C(N(CC)CC)C.C(O)=O>O1CCCC1.O>[C:55]([O:54][C:52]([NH:51][C@@H:18]([CH2:17][CH2:16][NH:15][C:13]([O:12][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][C@H:6]([NH:61][C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[C:5]([OH:69])=[O:4])=[CH:60][CH:59]=1)=[O:14])[C:19]([NH:21][C@H:22]([C:44]([NH:46][CH2:47][C:48]([NH2:50])=[O:49])=[O:45])[CH2:23][S:24][C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:20])=[O:53])([CH3:58])([CH3:57])[CH3:56]

参加物

6

反応物 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 89554995N-{(2S)-4-{[(4-{(2S)-3-(Allyloxy)-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}phenoxy)-carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]butanoyl}-S-trityl-L-cysteinylglycinamide

生成物 1

HCID 71557575N-[(2S)-2-[(tert-Butoxycarbonyl)amino]-4-{[(4-{(2S)-2-[(tert-butoxycarbonyl)amino]-2-carboxyethyl}phenoxy)carbonyl]amino}butanoyl]-S-trityl-L-cysteinylglycinamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

60 mg (0.031 mmol) of the compound from example 16A was dissolved in approx. 3 ml tetrahydrofuran. 22 μl (0.16 mmol) Triethylamine, 6 μl (0.16 mmol) formic acid and 4 mg (0.003 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 26 mg (86% 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 26 mg (86% of theory) product

出典と根拠

ORDレコード
ord-b82117382e444974bb20eac84c1cf340
出典データセット
uspto-grants-2016_04
特許番号
US09315543B2

反応ノート

読み込み中…