Formic Acid → HCID 42642567, compound

HRID 600321Notes

Reaction equation

HRID 600321 reaction equation
[C:1]([C@@H:3]([NH:22][C:23]([C@@H:25]1[CH2:30][CH2:29][CH2:28][CH2:27][N:26]1C(OC(C)(C)C)=O)=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([S:19]([CH3:21])=[O:20])[CH:12]=2)=[CH:7][CH:6]=1)#[N:2].C(O)=[O:39]>>[C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C@H:3]([NH:22][C:23]([C@@H:25]3[CH2:30][CH2:29][CH2:28][CH2:27][NH:26]3)=[O:24])[C:1]#[N:2])=[CH:6][CH:7]=2)=[CH:12][C:13]=1[S:19]([CH3:21])=[O:20])(=[O:39])[NH2:18]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 57999688HCID 57999688, compound

Product 1

HCID 42642567HCID 42642567, compound

Conditions

Temperature
50 °C

Procedure

A solution of (2S)-tert-butyl 2-((1S)-1-cyano-2-(4′-cyano-3′-(methylsulfinyl)biphenyl-4-yl)ethylcarbamoyl)piperidine-1-carboxylate (0.08 g) in formic acid (2 mL) was stirred and heated at 50° C. for 10 min. The mixture was evaporated and applied to a 10 g SCX column. The column was washed with methanol then eluted with 10% ammonia in methanol. The eluate was evaporated and the residue dissolved in isopropanol and precipitated with diethyl ether. The solid was collected, washed with diethyl ether and dried over magnesium sulfate. Purification by RPHPLC using aqueous 0.1% TFA afforded the major product as a colourless solid (0.027 g).

Workup

  1. customThe mixture was evaporated
  2. washThe column was washed with methanol
  3. washthen eluted with 10% ammonia in methanol
  4. customThe eluate was evaporated
  5. dissolutionthe residue dissolved in isopropanol
  6. customprecipitated with diethyl ether
  7. customThe solid was collected
  8. washwashed with diethyl ether
  9. dry with materialdried over magnesium sulfate
  10. customPurification by RPHPLC

Sources & evidence

ORD record
ord-707250983d9b4fd2be77d81da3b6e94b
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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