Formic Acid → HCID 59568580, compound

HRID 216987Notes

Reaction equation

HRID 216987 reaction equation
[C:1]([C@@H:3]([NH:22][C:23]([C:25]1([NH:31]C(=O)OC(C)(C)C)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:21]=[CH:20][C:14]3[CH2:15][S:16](=[O:19])(=[O:18])[CH2:17][C:13]=3[CH:12]=2)=[CH:7][CH:6]=1)#[N:2].C(O)=O>CO>[NH2:31][C:25]1([C:23]([NH:22][C@H:3]([C:1]#[N:2])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([C:11]3[CH:21]=[CH:20][C:14]4[CH2:15][S:16](=[O:19])(=[O:18])[CH2:17][C:13]=4[CH:12]=3)=[CH:9][CH:10]=2)=[O:24])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 59568629HCID 59568629, compound

Product 1

HCID 59568580HCID 59568580, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To tert-butyl [4-({(1S)-1-cyano-2-[4-(2,2-dioxido-1,3-dihydro-2-benzothiophen-5-yl)phenyl]ethyl}carbamoyl)tetrahydro-2H-pyran-4-yl]carbamate (Example 34, step (ii), 300 mg) was added formic acid (2 mL) and the mixture heated to 50° C. for 30 min. The mixture was allowed to cool to room temperature and then methanol (5 mL) was added and the mixture evaporated to give an oil. The crude mixture was purified by preparative HPLC (SunFire column) eluting with methanol/0.1% aqueous trifluoroacetic acid to afford a product which was then purified by chromatography on silica eluting with ethyl acetate to give the titled compound (82 mg).

Workup

  1. temperatureto cool to room temperature
  2. customthe mixture evaporated
  3. customto give an oil
  4. customThe crude mixture was purified by preparative HPLC (SunFire column)
  5. washeluting with methanol/0.1% aqueous trifluoroacetic acid
  6. customto afford a product which
  7. customwas then purified by chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-5a0f656f788b487796ce3cd7c84f4610
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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