p-Toluenesulfonic acid → 5-(9-(9-Fluorenylmethyloxycarbonyl)aminoxanthen-2-oxy)valeric Acid

HRID 1464587Notes

Reaction equation

HRID 1464587 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.O[CH:13]1[C:26]2[CH:25]=[C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH:23]=[CH:22][C:21]=2[O:20][C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2.[C:35]([NH-:52])([O:37][CH2:38][CH:39]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:45]2[C:40]1=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:36]>C(O)(=O)C>[CH:41]1[C:40]2[CH:39]([CH2:38][O:37][C:35]([NH:52][CH:13]3[C:26]4[CH:25]=[C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH:23]=[CH:22][C:21]=4[O:20][C:19]4[C:14]3=[CH:15][CH:16]=[CH:17][CH:18]=4)=[O:36])[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:45]=2[CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 10734020Pentanoic acid, 5-[(9-hydroxy-9H-xanthen-2-yl)oxy]-HCID 178514243HCID 178514243, compound

Product 1

HCID 118004825-(9-(9-Fluorenylmethyloxycarbonyl)aminoxanthen-2-oxy)valeric Acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of p-toluenesulfonic acid (0.15 g, 0.8 mmol) in glacial acetic acid (3 mL) was added dropwise at 25° C. over 15 minutes to a well-stirred suspsension of 5-(9-hydroxy-xanthen-2-oxy)valeric acid (2.0 g, 6.4 mmol) prepared as described above and Fmoc-amide (1.84 g, 8.2 mmol) in glacial acetic acid (50 mL). This mixture was stirred continuously and then filtered after 3 hours to collect a white solid which was washed with water (3×20 mL) and ehtyl ether (3×20 mL). The solid was dried in vacuo over P2O5 at 25° C. Yield: 2.35 g(61%, m.p. 210-211° C., Rf : 0.53 EtOAc/MeOh 5:1. NMR data and elemental analysis in accordance with structure. ##STR12##

Workup

  1. customprepared
  2. filtrationfiltered after 3 hours
  3. customto collect a white solid which
  4. washwas washed with water (3×20 mL) and ehtyl ether (3×20 mL)
  5. dry with materialThe solid was dried in vacuo over P2O5 at 25° C

Sources & evidence

ORD record
ord-9bd3db620f2244e9b21dadf62e992355
Source dataset
uspto-grants-1994_04
Patent number
US05306562

Reaction notes

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