Bromoform → 3-(Tert-butoxycarbonylamino)-1-(3-fluorophenoxy)cyclohexanecarboxylic acid

HRID 530849Notes

Reaction equation

[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.[F:16][C:17]1[CH:18]=[C:19](O)[CH:20]=[CH:21][CH:22]=1.[OH-:24].[Na+].C(Br)(Br)Br.C1[CH2:34][O:33]CC1>>[C:11]([O:10][C:9]([NH:8][CH:4]1[CH2:5][CH2:6][CH2:7][C:2]([O:1][C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([F:16])[CH:22]=2)([C:34]([OH:33])=[O:24])[CH2:3]1)=[O:15])([CH3:12])([CH3:14])[CH3:13]

Participants

Reactant 5

HCID 5558Bromoform

HCID 8028Tetrahydrofuran

HCID 97433-Fluorophenol

HCID 14798Sodium Hydroxide

HCID 44228975(3-Oxo-cyclohexyl)-carbamic acid tert-butyl ester

Product 1

HCID 679834013-(Tert-butoxycarbonylamino)-1-(3-fluorophenoxy)cyclohexanecarboxylic acidYield 3%

Procedure

To the mixture of tert-butyl 3-oxocyclohexylcarbamate (5 mmol, 1.065 g), 3-fluorophenol (5 mmol, 560 mg) and NaOH (25 mmol, 1 g) in THF at 0° C. was added bromoform (25 mmol, 2.2 mL) dropwise. The reaction mixture was allowed to warm to room temperature and stirred for overnight. The reaction mixture was concentrated. The product, 3-(tert-butoxycarbonylamino)-1-(3-fluorophenoxy)cyclohexanecarboxylic acid, was obtained (60 mg, 3% yield) after purification by reverse phase HPLC.

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-c2269e1e29fa45a2a0e96dc2c64f71ba
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09351965B2

Reaction notes

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