4-Ethoxy-3-(morpholine-4-carboxamido)benzene-1-sulfonyl chloride → (R)-benzyl 4-(dimethylamino)-3-(4-ethoxy-3-(morpholine-4-carboxamido)phenyl-sulfonamido)butanoate

HRID 1958735Notes

Reaction equation

HRID 1958735 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]([O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][C:22]=1[NH:31][C:32]([N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)=[O:33])[CH3:19]>>[CH3:17][N:15]([CH3:16])[CH2:14][C@H:2]([NH:1][S:27]([C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:18][CH3:19])=[C:22]([NH:31][C:32]([N:34]2[CH2:35][CH2:36][O:37][CH2:38][CH2:39]2)=[O:33])[CH:23]=1)(=[O:28])=[O:29])[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 27587604-Ethoxy-3-(morpholine-4-carboxamido)benzene-1-sulfonyl chlorideHCID 46223508(R)-benzyl 3-amino-4-(dimethylamino)butanoate

Product 1

HCID 86641228(R)-benzyl 4-(dimethylamino)-3-(4-ethoxy-3-(morpholine-4-carboxamido)phenyl-sulfonamido)butanoateYield 68%

Procedure

According to the method described in example S72a, (R)-benzyl 3-amino-4-(dimethylamino)butanoate (30 mg, 0.086 mmol) was reacted with 4-ethoxy-3-(morpholine-4-carboxamido)benzene-1-sulfonyl chloride to yield the title compound as a white solid (32 mg, 68%). MS ESI 549.3 [M+H]+, calcd for [C26H36N4O7S+H]+ 549.23

Sources & evidence

ORD record
ord-6dadd6ba4e0d4eddacf8c62886fd767a
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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