Acetyl chloride → HCID 13336145, compound

HRID 1583508Notes

Reaction equation

HRID 1583508 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18][SH:19])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:27](Cl)(=[O:29])[CH3:28]>C1COCC1>[C:27]([S:19][CH2:18][CH2:17][NH:16][C:14](=[O:15])[CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 9835457HCID 9835457, compound

Product 1

HCID 13336145HCID 13336145, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the stirred solution of 3-(benzyloxycarbonylamino)-N-(2-mercaptoethyl)propionamide (2 g) and triethylamine (0.8 g) in anhydrous THF (15 ml), acetyl chloride (0.6 g) is added dropwise under ice-water cooling. After the addition, the mixture is stirred for 30 minutes under ice-water cooling and additional 30 minutes at room temperature. The solution is filtered and the filtrate is concentrated in vacuo. The residue is dissolved in ethyl acetate (30 ml) and the solution is washed with saturated sodium bicarbonate solution, N hydrochloric acid and then saturated sodium chloride solution. The ethyl acetate solution is dried over anhydrous magnesium sulfate and concentrated in vacuo to give 1.6 g (70%) of the titled compound.

Workup

  1. additionAfter the addition
  2. filtrationThe solution is filtered
  3. concentrationthe filtrate is concentrated in vacuo
  4. dissolutionThe residue is dissolved in ethyl acetate (30 ml)
  5. washthe solution is washed with saturated sodium bicarbonate solution, N hydrochloric acid
  6. dry with materialThe ethyl acetate solution is dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-88bbf8ec53c64411a17556a8a8210b23
Source dataset
uspto-grants-1985_11
Patent number
US04552765

Reaction notes

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