Thioanisole → {3-Hydroxy-4-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-phenyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 1354850Notes

Reaction equation

HRID 1354850 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:48])[NH:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:39])[CH2:26][CH2:27][CH2:28][CH2:29][CH:30]4[CH:37]5[CH:33]([NH:34][C:35](=[O:38])[NH:36]5)[CH2:32][S:31]4)=[C:20]([O:40]CC4C=CC=CC=4)[CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C1(SC)C=CC=CC=1>C(O)(C(F)(F)F)=O.O>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:48])[NH:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:39])[CH2:26][CH2:27][CH2:28][CH2:29][CH:30]4[CH:37]5[CH:33]([NH:34][C:35](=[O:38])[NH:36]5)[CH2:32][S:31]4)=[C:20]([OH:40])[CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 7520ThioanisoleHCID 72447686{3-Benzyloxy-4-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-phenyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

Product 1

HCID 72447733{3-Hydroxy-4-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-phenyl}-carbamic acid 9H-fluoren-9-ylmethyl esterYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

{3-Benzyloxy-4-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-phenyl}-carbamic acid 9H-fluoren-9-ylmethyl ester (389) (0.28 g, 0.422 mmol) was dissolved in TFA (2 mL) and thioanisole (0.4 mL) was added. The mixture was shaken at room temperature in a Teflon septum capped 40 mL I-Chem vial for 3 h. LC-MS indicated complete de-benzylation at this point. The mixture was diluted with water (15 mL) and a pink/orange precipitate formed. Collection by filtration under reduced pressure followed by rinsing with water followed by drying under high vacuum for 16 h gave the desired product (390) as a pink/orange powder (0.152 g, 0.266 mmol, 63% yield). LC-MS (ESI): (exact mass: 572.21) m/e=573.1 [M+1]+.

Workup

  1. customcapped 40 mL I-Chem vial for 3 h
  2. customa pink/orange precipitate formed
  3. customCollection
  4. filtrationby filtration under reduced pressure
  5. washby rinsing with water
  6. customby drying under high vacuum for 16 h

Sources & evidence

ORD record
ord-6fbd608c2ca9430d97c23eaaa5e4d329
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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