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Water → Ethyl-4-phenoxycarbonylamino-1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate

HRID 1500604
Notes
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Reaction equation

HRID 1500604 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:7][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:10][C:11]=1[NH2:12])=[O:5])[CH3:2].N1C=CC=CC=1.[C:26](Cl)(=[O:34])[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH2:7][N:8]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:9][CH2:10][C:11]=1[NH:12][C:26]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:34])=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 592796481-tert-Butyl 3-ethyl 4-amino-5,6-dihydropyridine-1,3(2H)-dicarboxylate

Product 1

HCID 66685805Ethyl-4-phenoxycarbonylamino-1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Ethyl-4-amino-1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate (23.6 g) was dissolved in methylene chloride (460 ml), and pyridine (13 ml) and phenyl chlorocarbonate (15 ml) were added under ice cooling and the resultant mixture was stirred for one hour at the same temperature. To the reaction solution, water was added and the mixture was extracted with methylene chloride. After the organic layer was washed sequentially with 1 N hydrochloric acid and saturated saline solution in this order, the organic layer was dried over sodium sulfate, filtrated and concentrated under reduced pressure. To the resultant residue, diethyl ether was added to obtain a precipitate by filtration. The titled compound (10.57 g) was obtained as a colorless solid substance. Furthermore, the filtrate was concentrated under reduced pressure. Thereafter, the resultant residue was purified by medium-pressure silica gel column (solvent; ethyl acetate:hexane=10:90 to 50:50). The resultant crude crystal was washed with a solvent mixture of diethyl ether-hexane to obtain the titled compound (11.10 g) as a slightly yellow solid substance.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washAfter the organic layer was washed sequentially with 1 N hydrochloric acid and saturated saline solution in this order
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated under reduced pressure
  6. additionTo the resultant residue, diethyl ether was added
  7. customto obtain a precipitate
  8. filtrationby filtration

Sources & evidence

ORD record
ord-faf004d1f21d4e4fb69c55f12754528f
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09206173B2

Reaction notes

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