Ethyl bromoacetate → HCID 20331943, compound

HRID 2057489Notes

Reaction equation

HRID 2057489 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:8]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:7][N:6]=[N:5]1.C(N(CC)CC)C.Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>O1CCCC1>[C:28]([CH2:27][NH:1][CH2:2][CH2:3][N:4]1[C:8]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:7][N:6]=[N:5]1)([O:30][CH2:31][CH3:32])=[O:29]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 20331942HCID 20331942, compound

Product 1

HCID 20331943HCID 20331943, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 15.0 g. (56 mmol) of 1-(2-aminoethyl)-5-[(4-methoxybenzyl)thio]-1H-tetrazole in 70 ml. of dry tetrahydrofuran was added 7.7 ml. (56 mmol) of triethylamine, and 6.2 ml. (56 mmol) of ethyl bromoacetate. After stirring at room temperature for 15 hours, the mixture was filtered, and the filtrate was evaporated in vacuo to dryness. The residue was dissolved in 70 ml. of chloroform and decolorized with charcoal. The filtrate was chromatographed on silica gel, eluting with a gradient of 0-15% ethyl acetate in chloroform. Fractions containing product by thin layer chromatography were pooled and evaporated to dryness to give 12.5 g. (62% yield) of 1-[2-[[(carbethoxy)methyl]amino]ethyl]-5-[(4-methoxybenzyl)thio]-1H-tetrazole as a brown oil.

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was evaporated in vacuo to dryness
  3. dissolutionThe residue was dissolved in 70 ml
  4. customThe filtrate was chromatographed on silica gel
  5. washeluting with a gradient of 0-15% ethyl acetate in chloroform
  6. additionFractions containing product by thin layer chromatography
  7. customevaporated to dryness
  8. customto give 12.5 g

Sources & evidence

ORD record
ord-58d5e4d1a4564cb18ef5a044bac025a7
Source dataset
uspto-grants-1980_07
Patent number
US04210587

Reaction notes

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