1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 4632592, compound

HRID 1909824Notes

Reaction equation

HRID 1909824 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].N12CCCN=C1CCCCC2.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][C:26](Cl)=[O:27]>ClCCl>[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][C:26]([NH:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])=[O:27]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1623622-Thiopheneacetyl chlorideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 4632592HCID 4632592, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of glycine ethyl ester hydrochloride (21.77 g, 156 mmol) in anhydrous dichloromethane (260 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (55 mL, 368 mmol) was added under nitrogen, which addition turned the suspension clear. Then 2-thiopheneacetyl chloride (19.2 mL, 156 mmol) was added dropwise. After completion of the addition, the flask was warmed to room temperature and the mixture was stirred for 1 hour. Then it was washed with water (260 mL×3), dried and concentrated. A dark brown oil was obtained (31.77 g, yield 89%), which turned into a dark brown solid upon standing. 1H NMR (CDCl3, 500 MHz), δ=7.26 (dd, J=5.0, 1.0 Hz, 1H), 7.01-6.97 (m, 2H), 6.19 (s, 1H), 4.18 (q, J=7.0 Hz, 2H), 4.00 (d, J=5.0 Hz, 2H), 3.83 (s, 2H), 1.26 (t, J=7.0 Hz, 3H).

Workup

  1. additionwas added under nitrogen
  2. additionwhich addition
  3. additionAfter completion of the addition
  4. washThen it was washed with water (260 mL×3)
  5. customdried
  6. concentrationconcentrated
  7. customA dark brown oil was obtained (31.77 g, yield 89%), which

Sources & evidence

ORD record
ord-1eb4022f493c4da39ea87c5dc5be9f04
Source dataset
uspto-grants-2013_12
Patent number
US08598448B2

Reaction notes

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