Water → (S)-4-Amino-N-(2-(4'-carbamoyl-3'-fluorobiphenyl-4-yl)-1-cyanoethyl)tetrahydro-2H-pyran-4-carboxamide

HRID 216993Notes

Reaction equation

HRID 216993 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C@H:17]([NH:20][C:21]([C:23]3([NH:29]C(=O)OC(C)(C)C)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:22])[C:18]#[N:19])=[CH:12][CH:11]=2)=[CH:6][C:5]=1[F:37])(=[O:3])[NH2:2].O>C(#N)C>[NH2:29][C:23]1([C:21]([NH:20][C@H:17]([C:18]#[N:19])[CH2:16][C:13]2[CH:12]=[CH:11][C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:1](=[O:3])[NH2:2])=[C:5]([F:37])[CH:6]=3)=[CH:15][CH:14]=2)=[O:22])[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 962WaterHCID 59568571(S)-tert-Butyl 4-(2-(4'-carbamoyl-3'-fluorobiphenyl-4-yl)-1-cyanoethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Product 1

HCID 49783905(S)-4-Amino-N-(2-(4'-carbamoyl-3'-fluorobiphenyl-4-yl)-1-cyanoethyl)tetrahydro-2H-pyran-4-carboxamideYield 120.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-4-Amino-N-(2-(4′-carbamoyl-3′-fluorobiphenyl-4-yl)-1-cyanoethyl)tetrahydro-2H-pyran-4-carboxamide (Example 25, 212 mg) was suspended in acetonitrile (353 μL) and water (6.7 mL) and stirred under nitrogen at room temperature for 17.5 h. The solid was collected by filtration and dried under vacuum to give the titled compound as a solid (205 mg).

Workup

  1. filtrationThe solid was collected by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-ea02762da3a74966b9ddbabea8e2bc1a
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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