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Pyridine → Benzyloxycarbonyl-L-asparaginyl-Nepsilon-tert.butyloxycarbonyl-L-lysine

HRID 1284042
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HRID 1284042 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]([C:15]([OH:17])=[O:16])[NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N+](CC)(CC)CC)C1C=CC=CC=1.[N+](C1C=CC([O:41][C:42](=O)[C@H:43]([CH2:55][C:56](=[O:58])[NH2:57])[NH:44][C:45]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[O:46])=CC=1)([O-])=O.N1C=CC=CC=1>CN(C)C=O>[CH2:48]([O:47][C:45]([NH:44][C@H:43]([C:42]([NH:14][C@H:13]([C:15]([OH:17])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:41])[CH2:55][C:56](=[O:58])[NH2:57])=[O:46])[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1049PyridineHCID 17208BenzyltriethylammoniumHCID 2733283(2S)-2-amino-6-(((tert-butoxy)carbonyl)amino)hexanoic acidHCID 7021351Z-Asn-onp

생성물 1

HCID 22792312Benzyloxycarbonyl-L-asparaginyl-Nepsilon-tert.butyloxycarbonyl-L-lysine

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

51 g Nε-tert.butyloxycarbonyl-L-lysine were converted in a conventional manner into the benzyltriethylammonium salt and then stirred in 700 ml dimethylformamide with 81 g benzyloxycarbonyl-L-asparagine-4-nitrophenyl ester with the addition of 1 equivalent of pyridine for 48 hours at 20°. The residue left after vacuum evaporation was treated with ethyl acetate and potassium hydrogen sulfate solutions simultaneously; the thick precipitate formed was filtered off and then recrystallised from ethanol/petroleum ether. F = 174° - 175° (Z);[α]D20 = + 13.8° (c = 1.0; in pyridine). Yield = 70 g (71 % of the theoretical amount).

후처리

  1. waitThe residue left
  2. customafter vacuum evaporation
  3. additionwas treated with ethyl acetate and potassium hydrogen sulfate solutions simultaneously
  4. customthe thick precipitate formed
  5. filtrationwas filtered off
  6. customrecrystallised from ethanol/petroleum ether
  7. customF = 174° - 175° (Z)
  8. custom[α]D20 = + 13.8° (c = 1.0; in pyridine)

출처 및 근거

ORD 기록
ord-0a20e8faeede409f8ccf6455d7ba22bc
출처 데이터셋
uspto-grants-1976_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US03978035

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