Phenylacetylene → HCID 86641231, compound

HRID 1958742Notes

Reaction equation

Br[C:2]1[S:6][C:5]([S:7]([NH:10][C@@H:11]([CH2:23][N:24]([CH3:26])[CH3:25])[CH2:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])(=[O:9])=[O:8])=[CH:4][CH:3]=1.[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)#[CH:28]>>[CH3:25][N:24]([CH3:26])[CH2:23][C@H:11]([NH:10][S:7]([C:5]1[S:6][C:2]([C:28]#[C:27][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:3][CH:4]=1)(=[O:9])=[O:8])[CH2:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

Reactant 2

HCID 10821Phenylacetylene

HCID 59294388HCID 59294388, compound

Product 1

HCID 86641231HCID 86641231, compoundYield 87%

Procedure

According to the method described in example S76a, (R)-benzyl 3-(5-bromothiophene-2-sulfonamido)-4-(dimethylamino)butanoate was reacted with ethynylbenzene to give the title compound as a brown oil (55 mg, 87%). MS ESI 483.3 [M+H]+, calcd for [C25H26N2O4S2+H]+ 483.13.

Sources & evidence

ORD record: ord-c5d201e897e04e5dab17a1d55e400fd4
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410150B2

Reaction notes

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