[(tert-Butoxycarbonyl)amino](4-fluorophenyl)acetic acid → HCID 44546253, compound

HRID 1094344Notes

Reaction equation

HRID 1094344 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][CH2:11][C:12]2[CH:13]=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C(OC([NH:29][CH:30]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[C:31](O)=[O:32])=O)(C)(C)C>>[NH2:29][C@@H:30]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[C:31]([N:9]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1)[CH2:10][CH2:11][C:12]1[CH:13]=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=1)=[O:32]

Participants

3

Reactant 2

HCID 21901296[(tert-Butoxycarbonyl)amino](4-fluorophenyl)acetic acidHCID 58007591(3,4-Dimethyl-phenyl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine

Product 1

HCID 44546253HCID 44546253, compoundYield 13%

Procedure

In analogy to example 1, (3,4-dimethyl-phenyl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine (250 mg, 0.85 mmol, prepared as per example 1, step 3) and tert-butoxycarbonylamino-(4-fluoro-phenyl)-acetic acid (343 mg, 1.27 mmol, commercially available) were coupled together and resolved by chromatography on a chiral columnto afford the title compound (48 mg, 13%) as a pale yellow oil which crystallized upon standing MS m/e: 446.2 [M+H]+.

Sources & evidence

ORD record
ord-ad4b8218d996468a910e36648bd9af03
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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