Hydrochloric Acid → {[2-Fluoro-4-(4-fluoro-benzyloxy)-phenylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

HRID 1827439Notes

Reaction equation

HRID 1827439 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[NH2:17].Cl.[C:19]([NH:26][CH2:27][C:28](O)=[O:29])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C1(N=C=NC2CCCCC2)CCCCC1.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:22]([O:21][C:19](=[O:20])[NH:26][CH2:27][C:28](=[O:29])[NH:17][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:7][C:2]=1[F:1])([CH3:25])([CH3:23])[CH3:24]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 221378852-Fluoro-4-(4-fluoro-benzyloxy)-phenylamine

Product 1

HCID 69010933{[2-Fluoro-4-(4-fluoro-benzyloxy)-phenylcarbamoyl]-methyl}-carbamic acid tert-butyl esterYield 46%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-fluoro-4-(4-fluoro-benzyloxy)-phenylamine (1:1) hydrochloride (272 mg, 1 mmol), Boc-glycine (263 mg, 1.5 mmol), N,N′-dicylcohexylcarbodiimide (206 mg, 1 mmol) and pyridine (127 mg, 1.6 mmol) in ethyl acetate (6 mL) was stirred at room temperature for 3 h. After this time, the reaction mixture wa poured into sodium hydrogen carbonate (saturated), and the mixture extracted with ethyl acetate. The combined organic layers were then washed with brine and dried. Filtration and evaporation afforded the title compound (180 mg, 46%) as a light brown solid after chromatography on silica gel eluting with ethyl acetate:heptane (1:1 to 4:1). MS: m/e=393.1 (M++H).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe combined organic layers were then washed with brine
  3. customdried
  4. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-85fcbe89807147c5a9eb4c0857fea4a0
Source dataset
uspto-grants-2006_05
Patent number
US07053245B2

Reaction notes

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