4-t-Amylbenzenesulphonyl chloride → (R)-benzyl 4-(dimethylamino)-3-(4-pentylphenylsulfonamido)butanoate

HRID 1958721Notes

Reaction equation

HRID 1958721 reaction equation
[NH2:1][C@@H:2]([CH2:14][N:15]([CH3:17])[CH3:16])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[CH2:18]([C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)[CH2:19][CH2:20][CH2:21][CH3:22]>>[CH3:17][N:15]([CH3:16])[CH2:14][C@H:2]([NH:1][S:29]([C:26]1[CH:27]=[CH:28][C:23]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:24][CH:25]=1)(=[O:31])=[O:30])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

3

Reactant 2

HCID 1446254-t-Amylbenzenesulphonyl chlorideHCID 46223508(R)-benzyl 3-amino-4-(dimethylamino)butanoate

Product 1

HCID 86641219(R)-benzyl 4-(dimethylamino)-3-(4-pentylphenylsulfonamido)butanoateYield 25%

Procedure

According to the method described in example S20a, (R)-benzyl 3-amino-4-(dimethylamino)butanoate (27 mg, 0.086 mmol) was reacted with 4-pentylbenzene-1-sulfonyl chloride to yield the title compound as a white solid (9 mg, 25%). MS ESI 447.3 [M+H]+, calcd for [C24H34N2O4S+H]+ 447.22

Sources & evidence

ORD record
ord-bc589176c98746ae801ce22d1ee2b18d
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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