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

HRID 643262
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HRID 643262 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-05975c441f664452ac0030753f29e77e
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07700583B2

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