Hydrochloric Acid → Phenyl-(3S)-3-amino-4-phenylbut-1-enyl Sulfone Hydrochloride

HRID 2111534Notes

Reaction equation

HRID 2111534 reaction equation
C(OC([NH:8][CH:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:10]=O)=O)(C)(C)C.[C:19]1(S(CP(OCC)(=O)OCC)(=O)=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C[O-].[Na+].[CH:40]([S:42]([CH:45]=[CH2:46])(=[O:44])=[O:43])=C.[ClH:47]>CCOC(C)=O>[ClH:47].[C:19]1([CH:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C@H:9]([NH2:8])[CH:10]=[CH:40][S:42]([CH:45]=[CH:46][C@@H:9]([NH2:8])[CH:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:44])=[O:43])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6496Divinyl sulfoneHCID 5463171,1-Dimethylethyl N-(1-formyl-2-phenylethyl)carbamateHCID 10891636Diethyl ((phenylsulfonyl)methyl)phosphonateHCID 10942334Sodium Methoxide

Product 1

HCID 131727420Phenyl-(3S)-3-amino-4-phenylbut-1-enyl Sulfone HydrochlorideYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Boc-Phe-VS-Ph was prepared by reaction of Boc-Phe-H with diethyl phenylsulfonylmethanephosphonate in the presence of 2 N sodium methoxide, yield 85%. 1H-NMR (CDCl3) δ 1.3-1.4 (s, 9H, Boc), 2.9 (d, 2H, CH2-Phe), 4.4-4.5 (b, 1H, α-H), 4.6-4.7 (b, 1H, NH), 6.3 (d, 1H, CH═), 6.9-7.0 (dd, 1H, CH═), 7.1-7.3 (m, 5H, Ph), 7.5-7.8 (m, 5H, SO2-Ph). MS (FAB+) m/z 388 (M+1, 15%), 288 (M−Boc+1, 100%). Boc-Phe-VS-Ph was deblocked with 6.7 N HCl in EtOAc to give Phe-VS-Ph.HCl, yield 88%. 1H-NMR (DMSO-d6) δ 2.9-3.0 (m, 1H, CH2-Phe), 3.1-3.2 (m, 1H, CH2-Phe), 4.2 (b, 1H, α-H), 6.7-6.8 (m, 2H, CH═), 7.1-7.3 (m, 6H, CH═ and Ph), 7.6-7.8 (m, 5H, SO2-Ph), 8.6-8.8 (b, 2H, NH2). MS (FAB+) m/z 288 (M−Cl, 100%).

Sources & evidence

ORD record
ord-dcac3ed7583a4bb3b4b6c3164356477a
Source dataset
uspto-grants-2009_04
Patent number
US07521427B2

Reaction notes

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