(S)-Methyl 4-(1-aminoethyl)benzoate hydrochloride → Methyl 4-((1S)-1-{[5-chloro-2-(3,5-difluorophenoxy)benzoyl]amino}ethyl)benzoate

HRID 1293291Notes

Reaction equation

HRID 1293291 reaction equation
Cl.[NH2:2][C@H:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)[CH3:4].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([O:25][C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=2)=[C:20]([CH:24]=1)[C:21](O)=[O:22]>>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([O:25][C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[C:28]([F:33])[CH:27]=2)=[C:20]([CH:24]=1)[C:21]([NH:2][C@H:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)[CH3:4])=[O:22]

Participants

3

Reactant 2

HCID 57462942(S)-Methyl 4-(1-aminoethyl)benzoate hydrochlorideHCID 62784288HCID 62784288, compound

Product 1

HCID 69418813Methyl 4-((1S)-1-{[5-chloro-2-(3,5-difluorophenoxy)benzoyl]amino}ethyl)benzoate

Procedure

The title compound was prepared according to the procedure described in step 3 of Example 1 from methyl 4-[(1S)-1-aminoethyl]benzoate hydrochloride (step 3 of Example 5) and 5-chloro-2-(3,5-difluorophenoxy)benzoic acid (step 2): 1H-NMR (CDCl3) δ 8.14 (1H, d, J=2.8 Hz), 7.94 (2H, d, J=8.4 Hz), 7.45 (1H, dd, J=8.8, 2.8 Hz), 7.37 (1H, d, J=7.9 Hz), 7.28 (2H, d, J=8.4 Hz), 6.95 (1H, d, J=8.8 Hz), 6.58–6.68 (1H, m), 6.48–6.38 (2H, m), 5.31 (1H, dq, J=7.9, 7.0 Hz), 3.91 (3H, s), 1.49 (3H, d, J=7.0 Hz); MS (ESI) m/z 446 (M+H)+, 444 (M−H)−.

Sources & evidence

ORD record
ord-5da85ff9409540fba3f78aaebf65f1dc
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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