9-Fluorenylmethyl chloroformate → methyl (2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-(4-hydroxyphenyl)acetate

HRID 2414608Notes

Reaction equation

HRID 2414608 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]([NH2:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.C(N(CC)C(C)C)(C)C.Cl[C:24]([O:26][CH2:27][CH:28]1[C:40]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25]>ClCCl>[CH:39]1[C:40]2[CH:28]([CH2:27][O:26][C:24]([NH:12][C@H:4]([C:5]3[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=3)[C:3]([O:2][CH3:1])=[O:13])=[O:25])[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:35]=2[CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 343679-Fluorenylmethyl chloroformateHCID 81531DiisopropylethylamineHCID 4123006p-Hydroxyphenylglycine methyl ester

Product 1

HCID 86590203methyl (2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-(4-hydroxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° solution of 2.50 g (11.48 mmol) of amino-(4-hydroxy-phenyl)-acetic acid methyl ester (from Example 178) in 125 mL of dichloromethane was added 10 mL of N,N-diisopropylethylamine followed by 2.97 g (11.48 mmol) of 9-fluorenylmethyl chlorformate and the resulting mixture was stirred at 0° for 2 h and room temperature for 2 h. The reaction mixture was then concentrated and the residue was diluted with ethyl acetate and water. The organics were washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3) to provide methyl(2R)-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}(4-hydroxyphenyl)ethanoate as a white solid. Electrospray Mass Spec 404.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additionthe residue was diluted with ethyl acetate and water
  3. washThe organics were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3)

Sources & evidence

ORD record
ord-442089bfd4e441a4a751e5d6a34a4d1f
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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