Ammonium Chloride → HCID 90036487, compound

HRID 1055387Notes

Reaction equation

[CH2:1]([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:9]([C:13]1([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N+:26]([O-])=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-]>[Zn].CO>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[O:19][C:13]1([CH:9]([N:8]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10]([OH:12])=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 65 °C

Procedure

2-(Dibenzylamino)-2-(1-(2-nitrophenoxyl)cyclohexyl)acetic acid (0.8 g, 1.69 mmol, Eq: 1.00), NH4Cl (180 mg, 3.37 mmol, Eq: 2) and Zn (1.71 g, 26.1 mmol, Eq: 15.5) were combined with MeOH (35.0 mL) to give a grey suspension, and the mixture was heated to 65° C. for 90 min. The mixture was filtered through Celite, the filtrate was concentrated and partitioned between sat. aq. NaOAc and Et2O. The phases were separated and the organic layer washed with H2O, brine, dried over Na2SO4 and concentrated to afford 2-(1-(2-aminophenoxyl)cyclohexyl)-2-(dibenzylamino)acetic acid as light brown solid (0.6365 g, 85%). MS m/z 475.1 (MH+).

Workup

customto give a grey suspension
filtrationThe mixture was filtered through Celite
concentrationthe filtrate was concentrated
custompartitioned between sat. aq. NaOAc and Et2O
customThe phases were separated
washthe organic layer washed with H2O, brine
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-5db1cb2cedcb450d96d1e403e320b617
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394263B2

Reaction notes

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