Acetate → HCID 59541005, compound

HRID 1677504Notes

Reaction equation

HRID 1677504 reaction equation
[CH3:1][C:2]([CH3:40])([CH3:39])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:15]=[C:16]([N:20]4[CH2:24][CH2:23][C:22]([CH2:26][O:27]C(=O)C)([CH3:25])[CH2:21]4)[CH:17]=[CH:18][CH:19]=3)[N:12]=2)[N:7](COCC[Si](C)(C)C)[CH:6]=1)=[O:4].C([O-])(=O)C.CO.O>CCN(CC)CC>[OH:27][CH2:26][C:22]1([CH3:25])[CH2:23][CH2:24][N:20]([C:16]2[CH:15]=[C:14]([C:11]3[N:12]=[C:13]4[C:5]([C:3](=[O:4])[C:2]([CH3:39])([CH3:1])[CH3:40])=[CH:6][NH:7][C:8]4=[N:9][CH:10]=3)[CH:19]=[CH:18][CH:17]=2)[CH2:21]1

Participants

6

Reactant 4

HCID 175AcetateHCID 887MethanolHCID 962WaterHCID 67344993HCID 67344993, compound

Product 1

HCID 59541005HCID 59541005, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1-{2-[3-(3-Hydroxymethyl-3-methyl-pyrrolidin-1-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one was prepared following a similar procedure but using acetic acid 1-{3-[7-(2,2-dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-3-methyl-pyrrolidin-3-ylmethyl ester as starting material. In this reaction, the acetate was hydrolysed at the same time of the second step of the SEM hydrolysis by heated at reflux the hydrolysis intermediate in a 8/1/1 mixture of MeOH, H2O, and Et3N over the weekend. The product was obtained in 15% yield after SiO2 chromatography (hexanes/EtOAc 0-30% EtOAc).

Workup

  1. customIn this reaction
  2. temperatureby heated
  3. temperatureat reflux the hydrolysis intermediate

Sources & evidence

ORD record
ord-f31735014578496b9df4c7f3dd6cce26
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

Loading…