Triethylamine → HCID 86742767, compound

HRID 1383129Notes

Reaction equation

HRID 1383129 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH:7]([NH2:16])[C:8]1[N:9]=[C:10]([NH:13][CH:14]=[O:15])[S:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:25](Cl)(=[O:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:17])[CH:7]([C:8]1[N:9]=[C:10]([NH:13][CH:14]=[O:15])[S:11][CH:12]=1)[NH:16][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:31])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 54163863HCID 54163863, compound

Product 1

HCID 86742767HCID 86742767, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-45 °C

Procedure

In 100 ml of methylene chloride was dissolved 5.5 g (21.4 mmole) of 2-amino-2-(2-formylamino-1,3-thiazol-4-yl)acetic acid tert-butyl ester, and 2.165 g (21.4 mmole) of triethylamine was added thereto. Then, the mixture was cooled to -45° C. and a solution of 2.92 g (21.4 mmole) of ethyl chlorooxalate dissolved in 10 ml of methylene chloride was added dropwise thereto for 10 minutes. Then, a cooling bath was removed, and the mixture was stirred for 30 minutes. After the mixture was washed with water, it was dried over anhydrous magnesium sulfate and the solvent was evaporated to obtain 7.5 g of the oily title compound. (Yield: 98%)

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. customThen, a cooling bath was removed
  4. washAfter the mixture was washed with water, it
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e840051c77bb40b083e0f245eda1f5bb
Source dataset
uspto-grants-1989_02
Patent number
US04808711

Reaction notes

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