(2-Amino-5-bromophenyl)(2-fluorophenyl)methanone → 9H-fluoren-9-ylmethyl [2-({4-bromo-2-[(2-fluorophenyl)carbonyl]phenyl}amino)-2-oxoethyl]carbamate

HRID 1365054Notes

Reaction equation

HRID 1365054 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])=[O:10].Cl[C:19](=[O:39])[CH2:20][NH:21][C:22](=[O:38])[O:23][CH2:24][CH:25]1[C:37]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2>C(Cl)(Cl)Cl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:19](=[O:39])[CH2:20][NH:21][C:22](=[O:38])[O:23][CH2:24][CH:25]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=3[C:32]3[C:37]2=[CH:36][CH:35]=[CH:34][CH:33]=3)=[C:3]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 73865(2-Amino-5-bromophenyl)(2-fluorophenyl)methanoneHCID 11758879Fmoc-Gly-Cl

Product 1

HCID 577324349H-fluoren-9-ylmethyl [2-({4-bromo-2-[(2-fluorophenyl)carbonyl]phenyl}amino)-2-oxoethyl]carbamateYield 70.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A round-bottomed flask was charged with (2-amino-5-bromophenyl)(2-fluorophenyl)methanone (1.45 g), 9H-fluoren-9-ylmethyl (2-chloro-2-oxoethyl)carbamate (1.6 g) and chloroform (150 mL). The mixture was heated to reflux for 2 h then concentrated to dryness. The residue was taken up in a mixture of a saturated solution of sodium bicarbonate and ethyl acetate. The resulting solids were collected on a filter and washed first with water then with diethyl ether. Thorough air-drying provided 9H-fluoren-9-ylmethyl [2-({4-bromo-2-[(2-fluorophenyl)carbonyl]phenyl}amino)-2-oxoethyl]carbamate (2 g) as a light yellow powder. H1 NMR (d6-dmso): 10.8 (br s, 1H), 7.95 (d, 1H), 7.75-7.90 (m, 4H), 7.45-7.70 (m, 5H), 7.20-7.42 (m, 6H), 4.30 (d, 2H), 4.20 (t, 1H), 3.65 (d, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. concentrationthen concentrated to dryness
  4. additionThe residue was taken up in a mixture of a saturated solution of sodium bicarbonate and ethyl acetate
  5. customThe resulting solids were collected on
  6. filtrationa filter
  7. washwashed first with water

Sources & evidence

ORD record
ord-970db8cc30a44808b8dfa227af4a66a4
Source dataset
uspto-grants-2011_02
Patent number
US07888503B2

Reaction notes

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