Hydrochloric Acid → 4-{(1S)-1-[({2,5-dichloro-4-[(3-chlorophenyl)(tetrahydro-2H-pyran-2-yloxy)methyl]-3-thienyl}carbonyl)amino]ethyl}benzoic acid

HRID 870051Notes

Reaction equation

[Cl:1][C:2]1[S:3][C:4]([Cl:37])=[C:5]([CH:22]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=2)[O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[C:6]=1[C:7]([NH:9][C@H:10]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1)[CH3:11])=[O:8].Cl>>[Cl:1][C:2]1[S:3][C:4]([Cl:37])=[C:5]([CH:22]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=2)[O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[C:6]=1[C:7]([NH:9][C@H:10]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[CH3:11])=[O:8]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 57900986methyl 4-{(1S)-1-[({2,5-dichloro-4-[(3-chlorophenyl)(tetrahydro-2H-pyran-2-yloxy)methyl]-3-thienyl}carbonyl)amino]ethyl}benzoate

Product 1

HCID 249529244-{(1S)-1-[({2,5-dichloro-4-[(3-chlorophenyl)(tetrahydro-2H-pyran-2-yloxy)methyl]-3-thienyl}carbonyl)amino]ethyl}benzoic acid

Procedure

Methyl 4-{(1S)-1-[({2,5-dichloro-4-[(3-chlorophenyl)(tetrahydro-2H-pyran-2-yloxy)methyl]-3-thienyl}carbonyl)amino]ethyl}benzoate from Example 8, Step 4 (21.3 mg, 0.0365 mmol) was reacted under conditions similar to Example 1, Step 11. The reaction mixture was neutralized with 25% aq. NH4OAc (instead of an acidification with 1N HCl). The desired product was obtained as a white foam and was used without further purification. MS (−APCI): m/z 566 (M−1)−

Sources & evidence

ORD record: ord-2502ea08e0264d03adbcf151e90d683f
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969394B2

Reaction notes

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