(S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-N-undecylsuccinamic acid tert-butyl ester → (S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-N-undecylsuccinamic acid

HRID 2297319Notes

Reaction equation

HRID 2297319 reaction equation
C([O:5][C:6](=[O:41])[CH2:7][C@H:8]([NH:23][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])[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:10])(C)(C)C>C(O)(C(F)(F)F)=O.CO>[CH:30]1[C:29]2[CH:28]([CH2:27][O:26][C:24]([NH:23][C@H:8]([C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:10])[CH2:7][C:6]([OH:41])=[O:5])=[O:25])[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]=2[CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 1

HCID 53649195(S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-N-undecylsuccinamic acid tert-butyl ester

Product 1

HCID 54198668(S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-N-undecylsuccinamic acidYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

A solution of (S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-N-undecylsuccinamic acid tert-butyl ester (113 mg, 0.2 mmol) in TFA (2 ml) was stirred at room temperature for 30 min. After completion of the reaction, TFA was removed by evaporation in vacuo. Purification of the residue by silica gel column chromatography (using dichloromethane:methanol=9:1 as an eluent) gave (S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-N-undecylsuccinamic acid (101 mg, 99% yield) as a colorless amorphous solid.

Workup

  1. customwas removed by evaporation in vacuo
  2. customPurification of the residue by silica gel column chromatography (

Sources & evidence

ORD record
ord-c8c3450320594387af8708a5296c18b6
Source dataset
uspto-grants-2002_12
Patent number
US06489440B1

Reaction notes

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