Chloroacetyl chloride → HCID 68153562, compound

HRID 1946922Notes

Reaction equation

HRID 1946922 reaction equation
[NH2:1][C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=1)([C:5]1[CH:6]=[N:7][C:8]([O:11][CH:12]([F:14])[F:13])=[CH:9][CH:10]=1)[CH2:3][OH:4].Cl[CH2:23][C:24](Cl)=[O:25].C([O-])(C)(C)C.[K+]>C(O)(C)(C)C>[Br:21][C:17]1[CH:16]=[C:15]([C:2]2([C:5]3[CH:6]=[N:7][C:8]([O:11][CH:12]([F:14])[F:13])=[CH:9][CH:10]=3)[NH:1][C:24](=[O:25])[CH2:23][O:4][CH2:3]2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 23665647Potassium tert-butoxideHCID 68153304HCID 68153304, compound

Product 1

HCID 68153562HCID 68153562, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

In close analogy to the reaction sequence described for the preparation of intermediate X-1, the acylation of the (RS)-2-amino-2-(3-bromo-phenyl)-2-(6-difluoromethoxy-pyridin-3-yl)-ethanol with chloroacetylchloride followed by cyclisation with tert-butanol and potassium tert-butanolate yielded the (RS)-5-(3-bromo-phenyl)-5-(6-difluoromethoxy-pyridin-3-yl)-morpholin-3-one as a light yellow solid (1.6 g, 91% of theory). MS (ISP): m/z=400.9 [M+H]+.

Workup

  1. customIn close analogy to the reaction sequence described for the preparation of intermediate X-1

Sources & evidence

ORD record
ord-79cf20f295124b22a4e8480606d22bd4
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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