Trifluoroacetic acid → (5-Cyclopropylmethoxy-2-nitro-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester

HRID 1767588Notes

Reaction equation

HRID 1767588 reaction equation
C1([C:4]2[C:5]([C:16]([F:19])([F:18])[F:17])=[CH:6][C:7]([N+:13]([O-:15])=[O:14])=[C:8]([NH:10]OC)[CH:9]=2)CC1.Cl[C:21]1[C:22]([C:31](F)(F)F)=[CH:23]C([N+]([O-])=O)=C(N)C=1.[OH:35][CH2:36][CH:37]1[CH2:39][CH2:38]1.[OH-].[K+].[C:42]([OH:48])(C(F)(F)F)=[O:43]>CS(C)=O.C(Cl)Cl>[C:22]([O:48][C:42](=[O:43])[NH:10][C:8]1[CH:9]=[C:4]([O:35][CH2:36][CH:37]2[CH2:39][CH2:38]2)[C:5]([C:16]([F:17])([F:18])[F:19])=[CH:6][C:7]=1[N+:13]([O-:15])=[O:14])([CH3:31])([CH3:23])[CH3:21]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 75644CyclopropanemethanolHCID 27738135-Chloro-2-nitro-4-(trifluoromethyl)anilineHCID 223175455-Cyclopropyl-methoxy-2-nitro-4-trifluoromethyl-phenylamine

Product 1

HCID 69486933(5-Cyclopropylmethoxy-2-nitro-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

Compound A14 was prepared via the di-Boc-compound from 5-cyclopropyl-meth-oxy-2-nitro-4-trifluoromethyl-phenylamine [prepared by stirring commercially available 5-chloro-2-nitro-4-trifluoromethyl-phenylamine [CAS-No. 35375-74-7], (hydroxy-methyl)cyclopropane and KOH in DMSO at 23° C. for 4 days and at 60° C. for 7 days] (4.49 g, 16.3 mmol) and Boc20 (7.45 g, 34.1 mmol), followed by treatment with 2 eq. TFA in CH2Cl2 according to the general procedure A (method c).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-2322963e6e6542d49444e48152e0181c
Source dataset
uspto-grants-2007_06
Patent number
US07235547B2

Reaction notes

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