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Water → (2-trityl-2H-tetrazol-5-yl)-acetic acid

HRID 643262
ノート
印刷プレビュー

反応式

HRID 643262 の反応式
C([O:3][C:4](=[O:11])[CH2:5][C:6]1[N:7]=[N:8][NH:9][N:10]=1)C.[C:12](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.[OH-].[K+]>C1COCC1.C(O)C>[C:12]([N:8]1[N:9]=[N:10][C:6]([CH2:5][C:4]([OH:3])=[O:11])=[N:7]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 6456Trityl chlorideHCID 14797Potassium HydroxideHCID 543616Ethyl 1H-tetrazole-5-acetate

生成物 1

HCID 22405503(2-trityl-2H-tetrazol-5-yl)-acetic acid収率 15%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a mixture of (2H-tetrazol-5-yl)-acetic acid ethyl ester (2.0 g, 12.81 mmol), trityl chloride (3.7 g, 13.45 mmol) in dry THF (75 ml) was added TEA (3.7 ml). The resulting mixture was stirred for 18 hrs. at room temperature. Water (10 ml) was added and the precipitate filtered off, redissolved in EtOAc (25 ml) and washed with saturated aqueous ammonium chloride (2×15 ml). The organic phase was dried (Na2SO4), filtered and evaporated in vacuo. The residue was suspended in ethanol (150 ml) and potassium hydroxide (0.8 g, 13.45 mmol) dissolved in ethanol (100 ml) was added. The resulting mixture was stirred for 18 hrs. at room temperature. The precipitate was filtered off and dissolved in water (150 ml) and acidified with conc. HCl (use diluted HCl). The precipitate was filtered off and washed with diethyl ether and dried in vacuo at 50° C. affording 0.7 g (15%) of (2-trityl-2H-tetrazol-5-yl)-acetic acid as a solid.

後処理

  1. customat room temperature
  2. filtrationthe precipitate filtered off
  3. dissolutionredissolved in EtOAc (25 ml)
  4. washwashed with saturated aqueous ammonium chloride (2×15 ml)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. additionwas added
  9. stirringThe resulting mixture was stirred for 18 hrs
  10. customat room temperature
  11. filtrationThe precipitate was filtered off
  12. dissolutiondissolved in water (150 ml)
  13. filtrationThe precipitate was filtered off
  14. washwashed with diethyl ether
  15. customdried in vacuo at 50° C.

出典と根拠

ORDレコード
ord-05975c441f664452ac0030753f29e77e
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07700583B2

反応ノート

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