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

HRID 1284042
ノート
印刷プレビュー

反応式

HRID 1284042 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0a20e8faeede409f8ccf6455d7ba22bc
出典データセット
uspto-grants-1976_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US03978035

反応ノート

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