HCID 53836394, compound → HCID 54484501, compound

HRID 1576072Notes

Reaction equation

HRID 1576072 reaction equation
N(C([C:6]1[CH2:10][S:9][CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[C:7]=1[N:23]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:24](=[O:26])[CH3:25])=O)=[N+]=[N-].[C:32]([N:37](C1C(CCCCC(N2CCCCC2)=O)SCC=1N=C=O)C(=O)C)([O:34][CH2:35]C)=[O:33]>CO>[C:27]([N:23]([C:7]1[CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[S:9][CH2:10][C:6]=1[NH:37][C:32]([O:34][CH3:35])=[O:33])[C:24](=[O:26])[CH3:25])([O:29][CH2:30][CH3:31])=[O:28]

Participants

4

Reactant 2

HCID 53836394HCID 53836394, compoundHCID 54505490HCID 54505490, compound

Product 1

HCID 54484501HCID 54484501, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.8 g (.006 moles) of 4-azidocarbonyl-3-(N-carbethoxyacetamido)-2,5-dihydro-2-thiophenevaleric acid piperidide was dissolved in 50 ml. of methanol and brought slowly up to reflux over a 15 minute period. The reaction was allowed to proceed for 5 hrs. at this temperature. Formed as an intermediate in the reaction mixture was 3-(N-carbethoxyacetamido)-4-isocyanato-2,5-dihydro-2-thiophenevaleric acid piperidide. The methanol was then removed, and 2.33 g. (0.0056 mole, 85%) of 3-(N-carbethoxyacetamido)-4-carbomethoxyamino-2,5-dihydro-2-thiophenevaleric acid piperidide was obtained as a colorless oil.

Workup

  1. temperatureto reflux over a 15 minute period
  2. customFormed as an intermediate in the reaction mixture
  3. customThe methanol was then removed

Sources & evidence

ORD record
ord-6eeffa6d99ae4c81ad889732cc74e324
Source dataset
uspto-grants-1976_09
Patent number
US03979396

Reaction notes

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