Formic Acid → O-({(14S)-1-Azido-14-[(tert-butoxycarbonyl)amino]-13-oxo-3,6,9-trioxa-12-azahexadecan-16-yl}carbamoyl)-N-(tert-butoxycarbonyl)-L-tyrosine

HRID 630682노트

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HRID 630682 반응식
C([O:4][C:5](=[O:54])[C@H:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23](=[O:53])[NH:24][CH2:25][CH2:26][C@H:27]([NH:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C:28](=[O:44])[NH:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][N:41]=[N+:42]=[N-:43])=[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>[N:41]([CH2:40][CH2:39][O:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33][O:32][CH2:31][CH2:30][NH:29][C:28](=[O:44])[C@@H:27]([NH:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:26][CH2:25][NH:24][C:23]([O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][C@@H:6]([C:5]([OH:54])=[O:4])[NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])=[CH:21][CH:20]=1)=[O:53])=[N+:42]=[N-:43]

참가 물질

6

반응물 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 89555031Allyl-O-({(14S)-1-azido-14-[(tert-butoxycarbonyl)amino]-13-oxo-3,6,9-trioxa-12-azahexadecan-16-yl}carbamoyl)-N-(tert-butoxycarbonyl)-L-tyrosinate

생성물 1

HCID 71557730O-({(14S)-1-Azido-14-[(tert-butoxycarbonyl)amino]-13-oxo-3,6,9-trioxa-12-azahexadecan-16-yl}carbamoyl)-N-(tert-butoxycarbonyl)-L-tyrosine

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

276 mg (0.344 mmol) of the compound from example 23A was dissolved in approx. 15 ml tetrahydrofuran. 235 μl (1.68 mmol) Triethylamine, 63 μl (1.68 mmol) formic acid and 39 mg (0.034 mmol) tetrakis(triphenylphosphin)palladium(0) were added. The reaction mixture was stirred over night at room temperature. The reaction was diluted with approx. 20 ml water and twice extracted with approx. 20 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 167 mg (65% of theory) product.

후처리

  1. extractiontwice extracted with approx. 20 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 167 mg (65% of theory) product

출처 및 근거

ORD 기록
ord-0167495919cb4bc597c9f7dda5640434
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315543B2

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