Benzoic acid, 2,4-difluoro-, ethyl ester → HCID 68532439, compound

HRID 644201Notes

Reaction equation

HRID 644201 reaction equation
C([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[O:12][CH2:13][CH:14]([CH3:24])[CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])C.C(OC(=O)C1C=CC(F)=CC=1F)C.CC(CNC(OC(C)(C)C)=O)CO>>[C:20]([O:19][C:17]([NH:16][CH2:15][CH:14]([CH3:24])[CH2:13][O:12][C:6]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=1[C:4]([OH:25])=[O:3])=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 3

HCID 2737170Benzoic acid, 2,4-difluoro-, ethyl esterHCID 11424042Tert-butyl (3-hydroxy-2-methylpropyl)carbamateHCID 68535248Ethyl-2-(3-tert-butoxycarbonylamino-2-methylpropoxy)-4-fluorobenzoate

Product 1

HCID 68532439HCID 68532439, compoundYield 7%

Procedure

Using methods substantially equivalent to those described in Example 21-C, ethyl-2-(3-tert-butoxycarbonylamino-2-methylpropoxy)-4-fluorobenzoate was prepared from ethyl-2,4-difluorobenzoate and 2-methyl-3-tert-butoxycarbonylaminopropanol. The impure material was saponified using methods substantially equivalent to those described in Example 21-D to give 2-(3-tert-butoxycarbonylamino-2-methylpropoxy)-4-fluoro-benzoic acid (554 mg, 1.69 mmol, 7% for 2 steps after RPHPLC purification).

Sources & evidence

ORD record
ord-ae26553120e44b08ae648ae5ba6e7c9f
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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