Hydroxyamine hydrochloride → HCID 58032534, compound

HRID 405026Notes

Reaction equation

HRID 405026 reaction equation
C([O:5][C:6](=[O:36])[CH:7]([NH:20][C:21]([C:23]1[CH:24]=[C:25]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[CH:26]=[CH:27][CH:28]=1)=[O:22])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](O)=[N:16][OH:17])=[C:11]([F:19])[CH:10]=1)(C)(C)C.C(OC(=O)[CH:43]([NH:54][C:55]([C:57]1C=C(C2C=CC(C)=CC=2)C=CC=1)=[O:56])[CH2:44][C:45]1[CH:50]=[CH:49]C(C#N)=C(F)[CH:46]=1)(C)(C)C.Cl.[NH2:72]O.C([O-])(O)=O.[Na+]>C(O)C>[F:19][C:11]1[CH:10]=[C:9]([CH2:8][CH:7]([NH:20][C:21]([C:23]2[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)[CH:26]=[CH:27][CH:28]=2)=[O:22])[C:6]([OH:5])=[O:36])[CH:14]=[CH:13][C:12]=1[C:15]1[N:72]=[C:57]([C:55]([N:54]2[CH2:43][CH2:44][CH:45]([CH3:46])[CH2:50][CH2:49]2)=[O:56])[O:17][N:16]=1

Participants

6

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 66630458HCID 66630458, compoundHCID 178423745HCID 178423745, compound

Product 1

HCID 58032534HCID 58032534, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[3-Fluoro-4-(hydroxy-hydroxyimino-methyl)-phenyl]-2-[(4′-methyl-biphenyl-3-carbonyl)-amino]-propionic acid tert-butyl ester. A mixture of 3-(4-cyano-3-fluoro-phenyl)-2-[(4′-methyl-biphenyl-3-carbonyl)-amino]-propionic acid tert-butyl ester (10 g, 0.02 mol), hydroxylamine hydrochloride salt (7 g, 0.1 mol), and NaHCO3 (10 g, 0.12 mol) in ethanol (150 mL) was refluxed overnight. TLC showed the reaction was completed. The mixture were filtered and concentrated to give the title compound (10 g, 93% yield).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe mixture were filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bd77c3c212be49c3905177089c2e982e
Source dataset
uspto-grants-2014_06
Patent number
US08748412B2

Reaction notes

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