Hydrochloric Acid → HCID 21224235, compound

HRID 1584396Notes

Reaction equation

HRID 1584396 reaction equation
Cl.[C:2]([O:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].CN1CCOCC1.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[O:37]([C:44]1[CH:49]=[CH:48][C:47]([S:50][C:51]2([CH2:57][C:58](O)=[O:59])[CH2:56][CH2:55][O:54][CH2:53][CH2:52]2)=[CH:46][CH:45]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.Cl>C(Cl)Cl>[C:2]([O:6][NH:7][C:58](=[O:59])[CH2:57][C:51]1([S:50][C:47]2[CH:48]=[CH:49][C:44]([O:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[CH:45][CH:46]=2)[CH2:52][CH2:53][O:54][CH2:55][CH2:56]1)([CH3:5])([CH3:4])[CH3:3]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 21224122HCID 21224122, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 21224235HCID 21224235, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

O-(tert-Butyl)hydroxylamine hydrochloride (9.57 g), 4-methylmorpholine (15.64 ml), hydroxybenzotriazole (6.87 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (19.5 g) was added to a solution of 2-[4-(4-phenoxyphenylthio)-tetrahydropyran-4-yl]acetic acid (17.5 g) in methylene chloride (200 ml). After stirring for 3 hours at room temperature, 0.5 M hydrochloric acid (200 ml) was added to the mixture, and the mixture extracted with methylene chloride. The solvent was removed from the combined extracts under reduced pressure. Silica gel chromatography of the residue and elution with 35%-80% ethyl acetate/hexane gave N-tert-butoxy-2-[4-(4-phenoxyphenylthio)-tetrahydropyran-4-yl]-acetamide (15.3 g) as an oil, which can be used in the next reaction without further purification.

Workup

  1. extractionthe mixture extracted with methylene chloride
  2. customThe solvent was removed from the combined extracts under reduced pressure
  3. washSilica gel chromatography of the residue and elution with 35%-80% ethyl acetate/hexane

Sources & evidence

ORD record
ord-629648516ef143b4869e7413c7353179
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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