Ethanol ammonium hydroxide water → 3-Chloro-4-[2-(piperidin-4-yl)ethyloxy]phenylcarbonyl-2(S)-phenylsulfonylamino-beta-alanine

HRID 265877Notes

Reaction equation

C[O:2][C:3](=[O:42])[C@H:4]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH:29]2[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH:5]([Cl:15])[NH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].C(O)C.O.[NH4+].[OH-]>>[Cl:15][CH:5]([C@@H:4]([NH:16][S:17]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][CH:29]2[CH2:30][CH2:31][NH:32][CH2:33][CH2:34]2)=[CH:24][CH:25]=1)(=[O:18])=[O:19])[C:3]([OH:42])=[O:2])[NH:6][C:7]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:8]

Participants

Reactant 2

HCID 86596525Ethanol ammonium hydroxide water

HCID 867510853-Chloro-4-[2-(N-BOC-piperidin-4-yl)ethyloxy]phenylcarbonyl-2(S)-phenylsulfonylamino-beta-alanine Methyl Ester

Product 1

HCID 867510843-Chloro-4-[2-(piperidin-4-yl)ethyloxy]phenylcarbonyl-2(S)-phenylsulfonylamino-beta-alanineYield 36.2%

Procedure

Utilizing the procedure for convening 9-5 to 9-6, 15-5 (275 mg, 0.46 mmol) gave 15-6 (85 mg) after flash chromatography (silica, 10:1:1 ethanol/H2O/NH4OH). Rf 0.39 (silica, 10:1:1 ethanol/H2O/NH4OH).

Sources & evidence

ORD record: ord-f69f25ef34834dca9c798ed218b5ad02
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05648368

Reaction notes

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