Dicyclohexylcarbodiimide → HCID 12876467、化合物

HRID 1180361

反応式

HRID 1180361 の反応式
[NH:1]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C@H:2]([C:4]([NH:6][C@H:7]([C:9]([OH:11])=[O:10])[CH3:8])=[O:5])[CH3:3].C1COCC1.O[N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C:29]1=[O:34].C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[NH:1]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C@H:2]([C:4]([NH:6][C@H:7]([C:9]([O:11][N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C:29]1=[O:34])=[O:10])[CH3:8])=[O:5])[CH3:3]

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 7009583N-((Phenylmethoxy)carbonyl)-L-alanyl-L-alanineHCID 131726638THF N-hydroxysuccinimide

生成物 1

HCID 12876467HCID 12876467、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The active ester Z-Ala-Ala-OSu (1) was prepared according to a procedure described in Bodansky, M., Bodansky, A., The Practice of Peptide Synthesis 2nd Edition, Springer-Verlag. To a stirred solution of Z-Ala-Ala-OH (4.0 g, 13.6 mmol, obtained from Bachem) in 25 ml dry THF N-hydroxysuccinimide (1.56 g, 13.6 mmol) was added at 0° C. and the mixture was stirred for 10 minutes. A solution of dicyclohexylcarbodiimide (2.81 g, 13.6 mmol) in 3 ml dry THF was added. The mixture was stirred for 14 h, during which time it was allowed to warm to room temperature. The separated N,N′-dicyclohexylurea was removed by filtration and the solvent was evaporated in vacuo. The residue was twice recrystallized from isopropanol to give the active ester as a white solid (4.47 g, 84%) of m.p. 140° C.—TLC(MeOH/CHCl3, 1:50): Rf=0.5.—1H NMR (400 MHz, DMSO-d6): δ=1.20 (d, 3 H, J=7.0 Hz, CH3), 1.44 (d, 3 H, J=7.4 Hz, CH3), 2.79 (s, 4 H, 2×CH2), 4.04-4.10 (m, 1 H, CH), 4.63-4.69 (m, 1 H, CH), 4.96-5.04 (m, 2 H, CH2), 7.28-7.38 (m, 5 H, aryl-H), 7.45 (d, 1 H, J=7.8 Hz, NH), 8.58 (d, 1 H, J=7.0 Hz, NH).—MS (EI) m/z (%): 392 [M+H+], 414 [M+Na+], 430 [M+K+].

後処理

  1. stirringThe mixture was stirred for 14 h, during which time it
  2. customThe separated N,N′-dicyclohexylurea was removed by filtration
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was twice recrystallized from isopropanol

出典と根拠

ORDレコード
ord-064b7f36d430411bb986f6d0509968da
出典データセット
uspto-grants-2007_10
特許番号
US07279550B2

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