5-Chloro-2-(4-fluorophenoxy)benzoic acid → Methyl 4-((1S)-1-{[5-chloro-2-(4-fluorophenoxy)benzoyl]amino}ethyl)benzoate

HRID 1293221Notes

Reaction equation

HRID 1293221 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.[NH2:20][C@H:21]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)[CH3:22]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:6]([CH:10]=1)[C:7]([NH:20][C@H:21]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)[CH3:22])=[O:9]

Participants

3

Reactant 2

HCID 457924105-Chloro-2-(4-fluorophenoxy)benzoic acidHCID 57462942(S)-Methyl 4-(1-aminoethyl)benzoate hydrochloride

Product 1

HCID 57572299Methyl 4-((1S)-1-{[5-chloro-2-(4-fluorophenoxy)benzoyl]amino}ethyl)benzoate

Procedure

The title compound was prepared according to the procedure described in step 3 of Example 1 from 5-chloro-2-(4-fluorophenoxy)benzoic acid (step 2 of Example 67) and methyl 4-[(1S)-1-aminoethyl]benzoate hydrochloride (step 3 of Example 5): 1H-NMR (CDCl3) δ 8.16 (1H, d, J=2.6 Hz), 7.95 (2H, dd, J=6.6, 1.8 Hz), 7.88 (1H, d, J=7.4 Hz), 7.36–7.29 (3H, m), 7.23–6.96 (4H, m), 6.78 (1H, d, J=8.7 Hz), 5.32 (1H, dq, J=7.4, 6.9 Hz), 3.90 (3H, s), 1.51 (3H, d, J=6.9 Hz); MS (ESI) m/z 428 (M+H)+, 426 (M−H)−.

Sources & evidence

ORD record
ord-b648b38d89ec4ef7a73c897829330d3c
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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