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 630679노트

반응식

HRID 630679 반응식
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]

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b82117382e444974bb20eac84c1cf340
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315543B2

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