Di-tert-butyl dicarbonate → HCID 67072112, compound

HRID 1242410Notes

Reaction equation

HRID 1242410 reaction equation
[CH2:1](OC(=O)C(OC1C=C(C(F)(F)F)C=C(N)C=1)(C)C)C.[CH2:21]([O:23][C:24](=[O:47])[C:25]([O:28][C:29]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH:30]=1)([CH3:27])[CH3:26])[CH3:22].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(=O)([O-])O.[Na+]>O1CCOCC1.O>[CH2:21]([O:23][C:24](=[O:47])[C:25]([O:28][C:29]1[CH:34]=[C:33]([C:35]([F:37])([F:38])[F:36])[CH:32]=[C:31]([N:39]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH3:1])[CH:30]=1)([CH3:27])[CH3:26])[CH3:22]

Participants

6

Reactant 4

HCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 670722752-(3-Tert-butoxycarbonylamino-5-trifluoromethyl-phenoxy)-2-methyl-propionic acid ethyl esterHCID 670724252-(3-Amino-5-trifluoromethyl-phenoxy)-2-methyl-propionic acid ethyl ester

Product 1

HCID 67072112HCID 67072112, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

In analogy to the procedures described in example 5D], 5E] and 5F], 2-(3-amino-5-trifluoromethyl-phenoxy)-2-methyl-propionic acid ethyl ester was converted into 2-(3-tert-butoxycarbonylamino-5-trifluoromethyl-phenoxy)-2-methyl-propionic acid ethyl ester by treatment with di-tert-butyl dicarbonate and sodium hydrogen carbonate in dioxane/water at r.t., methylated at nitrogen to yield 2-[3-(tert-butoxycarbonyl-methyl-amino)-5-trifluoromethyl-phenoxy]-2-methyl-propionic acid ethyl ester and deprotected again to yield the title compound as light yellow oil.

Sources & evidence

ORD record
ord-db0fb11d2f05428dbccd72872e6ff284
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

Loading…