Hydroxylamine → HCID 178451239, compound

HRID 219881Notes

Reaction equation

HRID 219881 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][N:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:26][OH:27]>C(O)C>[C:1]([O:5][C:6](=[O:25])[CH2:7][N:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=[NH:17])[NH:26][OH:27])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 67529271HCID 67529271, compound

Product 1

HCID 178451239HCID 178451239, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of {tert-butoxycarbonyl-[3-cyanobenzyl]-amino}-acetic acid tert-butyl ester (3.5 g, 0.010 mol) in Ethanol (100 mL) under N2, was added hydroxylamine (1.66 mL, 0.0505 mol) in one portion. After being stirred at RT for 12 h, the reaction mixture was concentrated under reduced pressure to afford the title compound as a pale yellow viscous liquid (3.8 g, 99%). 1H NMR (DMSO-d6, 400 MHz) δ 9.59 (s, 1H), 7.53-7.56 (m, 2H), 7.29-7.33 (m, 1H), 7.24-7.26 (m, 1H), 5.76 (s, 2H), 4.37-4.39 (s, 2H), 3.74 (s, 2H), 1.35-1.37 (s, 18H). LC/MS (Method A): 380.0 (M+H)+. HPLC (Method B) Rt 5.91 min (Purity: 90.3%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-32d10d9267b44743bf1f625f7644052b
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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