5-(Isoxazol-3-yl)thiophene-2-sulfonyl chloride → (R)-benzyl 4-(dimethylamino)-3-(5-(isoxazol-3-yl)thiophene-2-sulfonamido)butanoate

HRID 1958720Notes

Reaction equation

HRID 1958720 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].[O:18]1[CH:22]=[CH:21][C:20]([C:23]2[S:27][C:26]([S:28](Cl)(=[O:30])=[O:29])=[CH:25][CH:24]=2)=[N:19]1>>[CH3:17][N:15]([CH3:16])[CH2:14][C@H:2]([NH:1][S:28]([C:26]1[S:27][C:23]([C:20]2[CH:21]=[CH:22][O:18][N:19]=2)=[CH:24][CH:25]=1)(=[O:29])=[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 27971805-(Isoxazol-3-yl)thiophene-2-sulfonyl chlorideHCID 46223508(R)-benzyl 3-amino-4-(dimethylamino)butanoate

Product 1

HCID 86641218(R)-benzyl 4-(dimethylamino)-3-(5-(isoxazol-3-yl)thiophene-2-sulfonamido)butanoateYield 84%

Procedure

According to the method described in example S20a, (R)-benzyl 3-amino-4-(dimethylamino)butanoate (27 mg, 0.086 mmol) was reacted with 5-(isoxazol-3-yl)thiophene-2-sulfonyl chloride to yield the title compound as a white solid (38 mg, 84%). MS ESI 450.2 [M+H]+, calcd for [C20H23N3O5S2+H]+ 450.11

Sources & evidence

ORD record
ord-d97f546337594cf8812b8f244406f68c
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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