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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Formic Acid → N-(tert-Butoxycarbonyl)-O-{[(4R,7S)-4-carbamoyl-13,13-dimethyl-6,11-dioxo-1,1,1-triphenyl-12-oxa-2-thia-5,10-diazatetradecan-7-yl]carbamoyl}-L-tyrosine

HRID 630677
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HRID 630677 반응식
C([O:4][C:5](=[O:65])[C@H:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23](=[O:64])[NH:24][C@@H:25]([CH2:54][CH2:55][NH:56][C:57](=[O:63])[O:58][C:59]([CH3:62])([CH3:61])[CH3:60])[C:26](=[O:53])[NH:27][C@H:28]([C:50](=[O:52])[NH2:51])[CH2:29][S:30][C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([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)=[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:65])=[O:4])[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][C:23](=[O:64])[NH:24][C@@H:25]([CH2:54][CH2:55][NH:56][C:57](=[O:63])[O:58][C:59]([CH3:60])([CH3:62])[CH3:61])[C:26](=[O:53])[NH:27][C@H:28]([C:50](=[O:52])[NH2:51])[CH2:29][S:30][C:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:20][CH:21]=1)=[O:9])([CH3:12])([CH3:13])[CH3:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 89555014Allyl-N-(tert-butoxycarbonyl)-O-{[(4R,7S)-4-carbamoyl-13,13-dimethyl-6,11-dioxo-1,1,1-triphenyl-12-oxa-2-thia-5,10-diazatetradecan-7-yl]carbamoyl}-L-tyrosinate

생성물 1

HCID 71557416N-(tert-Butoxycarbonyl)-O-{[(4R,7S)-4-carbamoyl-13,13-dimethyl-6,11-dioxo-1,1,1-triphenyl-12-oxa-2-thia-5,10-diazatetradecan-7-yl]carbamoyl}-L-tyrosine

시약·촉매·용매

2
HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

4.91 g (5.40 mmol) of the compound from example 14A was dissolved in approx. 110 ml tetrahydrofuran. 3.8 ml (27 mmol) Triethylamine, 1.02 ml (27 mmol) formic acid and 0.62 g (0.54 mmol) tetrakis(triphenylphosphin)palladium(0) were added. The reaction mixture was stirred over night at room temperature. The reaction was diluted with approx. 60 ml water and twice extracted with approx. 50 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 dissolved in dichloromethane and chromatographed over approx. 500 ml silica gel. Solvents used were dichloromethane, dichloromethane/methanol 40/1 and dichloromethane/methanol 1/1. The product-containing fractions were combined and concentrated to dryness under reduced pressure. The raw product was further purified by preparative RP-HPLC on a C18 column with a water/methanol gradient to yield 1.96 g (42% of theory) product.

후처리

  1. extractiontwice extracted with approx. 50 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. dissolutionThe raw product was dissolved in dichloromethane
  6. customchromatographed over approx. 500 ml silica gel
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe raw product was further purified by preparative RP-HPLC on a C18 column with a water/methanol gradient
  9. customto yield 1.96 g (42% of theory) product

출처 및 근거

ORD 기록
ord-c29f398dcfe64ab0aa2fd3c1bc7de992
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09315543B2

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