Sodium Hydroxide → HCID 54010535, compound

HRID 1576073Notes

Reaction equation

HRID 1576073 reaction equation
[C:1]([N:6]([C:10]1[CH:11]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:25])[S:12][CH2:13][C:14]=1[NH:15][C:16]([O:18][CH3:19])=[O:17])C(=O)C)([O:3][CH2:4][CH3:5])=[O:2].[OH-].[Na+]>O1CCCC1>[C:1]([NH:6][C:10]1[CH:11]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]([N:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)=[O:25])[S:12][CH2:13][C:14]=1[NH:15][C:16]([O:18][CH3:19])=[O:17])([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54484501HCID 54484501, compound

Product 1

HCID 54010535HCID 54010535, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.1 g (.000219 moles) of 3-(N-carbethoxyacetamido)-4-carbomethoxyamino-2,5-dihydro-2-thiophenevaleric acid piperidide was dissolved in 10 ml of tetrahydrofuran, and to this solution, 2 ml of 1 N sodium hydroxide was added. The heterogeneous solution was stirred for 2 hrs. and was then worked up immediately. Tetrahydrofuran was removed under vacuum, and the aqueous basic residue was partitioned between 30 ml of water and 20 ml of dichloromethane. The aqueous phase was extracted three times with 20 ml portions of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and evaporated, giving 0.08 g (0.000196 moles, 90%) of 3-carbethoxyamino-4-carbomethoxyamino-2,5-dihydro-2-thiophenevaleric acid piperidide. Upon trituration with pet. ether, the product was obtained as a solid which could be recrystallized from ethyl acetate to give white crystals; m.p. 120°-122°.

Workup

  1. customTetrahydrofuran was removed under vacuum
  2. customthe aqueous basic residue was partitioned between 30 ml of water and 20 ml of dichloromethane
  3. extractionThe aqueous phase was extracted three times with 20 ml portions of dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-230eedf2ddef485e896a33ba6844d497
Source dataset
uspto-grants-1976_09
Patent number
US03979396

Reaction notes

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