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4-Methylmorpholine → Z-Lys(Tos)-Glu(OBzl)-OBzl

HRID 1632403
ノート
印刷プレビュー

反応式

HRID 1632403 の反応式
[NH2:1][C@H:2]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:3][CH2:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH:25]([C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46])[C@H:26]([C:42](O)=[O:43])[CH2:27][CH2:28][CH2:29][CH2:30][NH:31][S:32]([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33].CN1CCOCC1.ClC(OCC(C)C)=O>CN(C)C=O.O1CCCC1.C(OCC)C.C(N(CC)CC)C>[NH:25]([C:45]([O:47][CH2:48][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)=[O:46])[C@H:26]([C:42]([NH:1][C@H:2]([C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[CH2:3][CH2:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:43])[CH2:27][CH2:28][CH2:29][CH2:30][NH:31][S:32]([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 3037947L-Glutamic acid dibenzyl esterHCID 15580620L-Lysine,N6-[(4-methylphenyl)sulfonyl]-N2-[(phenylmethoxy)carbonyl]-

生成物 1

HCID 131713857Z-Lys(Tos)-Glu(OBzl)-OBzl

試薬・触媒・溶媒 4

HCID 3283
Diethyl Ether
溶媒
HCID 6228Dimethylformamide溶媒2 回
HCID 8028Tetrahydrofuran溶媒
HCID 8471Triethylamine溶媒

反応条件

温度
-15 °C

実験手順

4.18 Grams of H-Glu(OBzl)-OBzl.Tos was dissolved in 30 ml of dimethylformamide (DMF), then 1.21 ml of triethylamine (TEA) was added and the mixture was stirred under cooling. On the other hand, 4.35 g of Z-Lys(Tos)-OH was dissolved in 30 ml of tetrahydrofuran (THF), and 0.98 ml of N-methylmorpholine was added thereto, then this mixture was cooled to -15° C. and under stirring condition 1.27 ml of isobutyl chloroformate was added dropwise. 30 Seconds after the addition, then the cooled DMF solution mentioned above was added thereto and this mixture was stirred at 0° C. for 5 minutes, then at 40° C. in a water bath for 1 minute, further at 15° C. for 30 minutes. THF and DMF were removed from the reaction mixture under a reduced pressure, the residue thus obtained was extracted with ethyl acetate. The extract was washed with 1N-citric acid, a saturated aqueous solution of sodium chloride, a saturated aqueous solution of sodium hydrogencarbonate then a saturated aqueous solution of sodium chloride in this order, then was dried with anhydrous sodium sulfate, and ethyl acetate was removed distillation. The oily residue obtained was solidified by adding ethyl ether and reprecipitated from ethyl acetate-ether to obtain 5.37 g of the desired product.

後処理

  1. temperatureunder cooling
  2. additionwas added dropwise
  3. addition30 Seconds after the addition
  4. additionabove was added
  5. stirringthis mixture was stirred at 0° C. for 5 minutes
  6. waitfurther at 15° C. for 30 minutes
  7. customTHF and DMF were removed from the reaction mixture under a reduced pressure
  8. customthe residue thus obtained
  9. extractionwas extracted with ethyl acetate
  10. washThe extract was washed with 1N-citric acid
  11. dry with materiala saturated aqueous solution of sodium chloride, a saturated aqueous solution of sodium hydrogencarbonate then a saturated aqueous solution of sodium chloride in this order, then was dried with anhydrous sodium sulfate, and ethyl acetate
  12. customwas removed
  13. distillationdistillation
  14. customThe oily residue obtained
  15. customreprecipitated from ethyl acetate-ether

出典と根拠

ORDレコード
ord-7636de50eefe455dba6c7bd5500ecc03
出典データセット
uspto-grants-1984_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04474754

反応ノート

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