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

HRID 1197194Notes

Reaction equation

HRID 1197194 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]([NH2:52])([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 7363019-Fluorenylmethyl carbamateHCID 10734020Pentanoic acid, 5-[(9-hydroxy-9H-xanthen-2-yl)oxy]-

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 (30 mg, 0.015 mmol) in glacial acetic acid (3 mL) was added dropwise at 25° C. over 15 minutes to a solution of 5-(9-hydroxyxanthen-2-oxy)valeric acid (0.2 g, 0.64 mmol) prepared as described above and Fmoc-NH2 (184 mg, 0.76 mmol) in glacial acetic acid (12 mL). This mixture was stirred continuously for 14 hours, filtered, and the resultant white solid washed with water (3×5 mL) and n-hexane (2×5 mL). The solid was dried in vacuo over P2O5 at 25° C. for 6 hours. Yield: 200 mg (69%), TLC-pure Rf : 0.53 EtOAc/MeOH 10:2. 1H-NMR (CDCl3, 300 MHz) δ7.76 (d, 7.4 Hz 2H), 7.59 (d, 7.4, 2H), 7.40 (t,J=7.4, 2H), 7.31 (t,J=7.4 2H), 4.69 (s, broad, 1H), 4.40 (d, J=6.9, 2H), 4.24 (t,J=6.9, 1H).

Workup

  1. customprepared
  2. filtrationfiltered
  3. washthe resultant white solid washed with water (3×5 mL) and n-hexane (2×5 mL)
  4. dry with materialThe solid was dried in vacuo over P2O5 at 25° C. for 6 hours

Sources & evidence

ORD record
ord-f58af98ab6454006a73f1a95c43e2939
Source dataset
uspto-grants-1992_05
Patent number
US05117009

Reaction notes

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