Triethylamine → N-(tert-butoxy)-2-[1-(4-phenoxyphenylthio)cyclopent-1-yl]-acetamide

HRID 1584395Notes

Reaction equation

HRID 1584395 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2([CH2:20][C:21]([OH:23])=O)[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:25]([O:29][NH2:30])([CH3:28])([CH3:27])[CH3:26].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:25]([O:29][NH:30][C:21](=[O:23])[CH2:20][C:15]1([S:14][C:11]2[CH:12]=[CH:13][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:9][CH:10]=2)[CH2:16][CH2:17][CH2:18][CH2:19]1)([CH3:28])([CH3:27])[CH3:26]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 212241652-[1-(4-Phenoxyphenylthio)-cyclopent-1-yl]-acetic acid

Product 1

HCID 21224113N-(tert-butoxy)-2-[1-(4-phenoxyphenylthio)cyclopent-1-yl]-acetamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

The 2-[1-(4-phenoxyphenylthio)-cyclopent-1-yl]-acetic acid obtained in Example 5 was dissolved in methylene chloride (8 ml) and treated with 4 -dimethylaminopyridine (180 mg), O-(tert-butyl) hydroxylamine hydrochloride (360 mg), triethylamine (540 μL), pyridine (400 μL), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (750 mg). After stirring overnight the reaction mixture was partitioned between ethyl acetate and water, the organic layer separated, and the solvent removed under reduced pressure. Preparative TLC of the residue and elution with 2:1 hexane/ethyl acetate gave N-(tert-butoxy)-2-[1-(4-phenoxyphenylthio)cyclopent-1-yl]-acetamide (270 mg) as a white foam, which can be used in the next reaction without further purification.

Workup

  1. customwas partitioned between ethyl acetate and water
  2. customthe organic layer separated
  3. customthe solvent removed under reduced pressure
  4. washPreparative TLC of the residue and elution with 2:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-90e8552d1e1b40fdaff4e76175dbaefe
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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