Sulfuric Acid → Z-Gln(Trt)-OH

HRID 1110192

反応式

HRID 1110192 の反応式
C(OC(=O)C)(=O)C.[NH:8]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][CH2:11][C:12](=[O:14])[NH2:13].[C:28]1([C:34]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.S(=O)(=O)(O)O>C(O)(=O)C.O>[NH:8]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][CH2:11][C:12](=[O:14])[NH:13][C:34]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 6457TriphenylcarbinolHCID 7918Acetic AnhydrideHCID 75855L-Glutamine, N2-[(phenylmethoxy)carbonyl]-

生成物 1

HCID 10962399Z-Gln(Trt)-OH

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

1.1 ml of acetic anhydride (12 mmol) are added to a mixture of 2.8 g of Z-Gln-OH (10 mmol), 5.2 g of triphenylmethanol (20 mmol) in 30 ml of acetic acid, and the mixture is stirred at 50° for 15 minutes. Then 0.05 ml of conc. sulfuric acid (about 1 mmol) is added, resulting in a clear yellow solution after a few minutes. After 2 hours, the solution is added dropwise to 500 ml of water, while stirring and cooling in ice, and the precipitate is filtered off and thoroughly washed with water. The moist material is dissolved in ethyl acetate, the aqueous phase is separated off, and the organic phase is washed once with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure to 20 g. Z-Gln(Trt)-OH is crystallized by addition of hexane in portions, m.p. 161°-162°.

後処理

  1. customresulting in a clear yellow solution after a few minutes
  2. waitAfter 2 hours
  3. stirringwhile stirring
  4. temperaturecooling in ice
  5. filtrationthe precipitate is filtered off
  6. washthoroughly washed with water
  7. dissolutionThe moist material is dissolved in ethyl acetate
  8. customthe aqueous phase is separated off
  9. washthe organic phase is washed once with a saturated aqueous sodium chloride solution
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated under reduced pressure to 20 g
  12. customZ-Gln(Trt)-OH is crystallized by addition of hexane in portions, m.p. 161°-162°

出典と根拠

ORDレコード
ord-ef8e9dcc58d749819f27a189ae70c37e
出典データセット
uspto-grants-1994_06
特許番号
US05324833

関連ノート

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