Triethylamine → HCID 86733531, compound

HRID 1657893Notes

Reaction equation

HRID 1657893 reaction equation
[CH3:1][O:2][C:3]([CH:5]([N:9]1[CH:12]([S:13][N:14]2[C:18](=[O:19])[CH2:17][CH2:16][C:15]2=[O:20])[CH:11]([NH:21][C:22](=[O:30])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:10]1=[O:31])[C:6]([CH3:8])=[CH2:7])=[O:4].C(N(CC)CC)C>O1CCCC1>[CH3:1][O:2][C:3]([C:5]([N:9]1[CH:12]([S:13][N:14]2[C:18](=[O:19])[CH2:17][CH2:16][C:15]2=[O:20])[CH:11]([NH:21][C:22](=[O:30])[CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:10]1=[O:31])=[C:6]([CH3:8])[CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86733532HCID 86733532, compound

Product 1

HCID 86733531HCID 86733531, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2.25 g (5 mmoles) of 1-(1-methoxycarbonyl-2-methylprop-2-enyl)-3-phenylacetamido-4-succinimidothio-azetidin-2-one (prepared as described in Example 2) and 1.4 ml (10 mmoles) of triethylamine in 100 ml of tetrahydrofuran was stirred at 65 °C for 25 minutes. The reaction mixture was evaporated, treated with 25 ml of ethyl acetate and evaporated once more. The residual foam was dissolved in 50 ml of ethyl acetate, treated with charcoal and concentrated to a small volume. The desired product crystallized upon cooling. There was obtained 1-(1-methoxycarbonyl-2-methylpropenyl)-3-phenylacetamido-4-succinimidothio-azetidin-2-one.

Workup

  1. customThe reaction mixture was evaporated
  2. additiontreated with 25 ml of ethyl acetate
  3. customevaporated once more
  4. dissolutionThe residual foam was dissolved in 50 ml of ethyl acetate
  5. additiontreated with charcoal
  6. concentrationconcentrated to a small volume
  7. customThe desired product crystallized
  8. temperatureupon cooling

Sources & evidence

ORD record
ord-888798039b574fd3be98ca83c7ac8068
Source dataset
uspto-grants-1976_06
Patent number
US03962277

Reaction notes

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