Ethyl orthoformate → HCID 22827147, compound

HRID 1462462Notes

Reaction equation

HRID 1462462 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]([CH3:24])[C@@H:13]2C(=O)[CH2:17][CH2:16][CH2:15][C@H:14]2[N:20]2[CH2:23][CH2:22][CH2:21]2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].ClC1C=C(CC(N(C)[C@@H]2C(=O)CCC[C@H]2N2CCCC2)=O)C=CC=1Cl.C(O[CH:53]([O:57][CH2:58][CH3:59])[O:54][CH2:55][CH3:56])C>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]([CH3:24])[C@@H:13]2[C:53]([O:54][CH2:55][CH3:56])([O:57][CH2:58][CH3:59])[CH2:17][CH2:16][CH2:15][C@H:14]2[N:20]2[CH2:23][CH2:22][CH2:21]2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 22827146HCID 22827146, compoundHCID 22827148HCID 22827148, compound

Product 1

HCID 22827147HCID 22827147, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedure of Example 3, substituting trans-(±)-3,4-difluoro-N-methyl-N-[6-oxo-2-(1-azetidinyl)cyclohexyl]benzeneacetamide for the trans-(±)-3,4-dichloro-N-methyl-N-[6-oxo-2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide in 50 ml of dry ethanol instead of methanol and 5.0 ml of triethylorthoformate instead of trimethylorthoformate, there is formed as product trans-(±)-3,4-difluoro-N-methyl-N-[6,6-diethoxy-2-(1-azetidinyl)cyclohexyl]benzeneacetamide, which is converted to a hydrochloride salt.

Sources & evidence

ORD record
ord-90c93ab025004fe6a95a1575b1591915
Source dataset
uspto-grants-1984_07
Patent number
US04460600

Reaction notes

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