p-Bromobenzenesulfonyl chloride → HCID 59192605, compound

HRID 1696884Notes

Reaction equation

HRID 1696884 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH:14]([NH2:19])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(NC(C)C)(C)C.[Br:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>>[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH:14]([NH:19][S:35]([C:32]3[CH:33]=[CH:34][C:29]([Br:28])=[CH:30][CH:31]=3)(=[O:37])=[O:36])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 7912DiisopropylamineHCID 59192558(5-Amino-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester

Product 1

HCID 59192605HCID 59192605, compoundYield 61%

Procedure

Starting with (5-amino-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (example 1-1, method A, 3rd step) (0.500 g, 1.8 mmol), diisopropylamine (0.553 g, 2.1 mmol) and 4-bromobenzenesulfonyl chloride (0.465 g, 1.8 mmol), using the method analogous to the one described for example 1-1, method A, 4th step, [5-(4-bromo-benzenesulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester (0.53 g, 61%) was obtained. MS cald. for C22H26BrNO5S 495, obsd. 496 [(M+H)+].

Sources & evidence

ORD record
ord-b1ab3e6abb4a445fa4c3f2f1bbeee87b
Source dataset
uspto-grants-2012_04
Patent number
US08163781B2

Reaction notes

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