Acetonitrile → HCID 59243619, compound

HRID 425033Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of cyclopentyl(2S)-4-[(4-bromophenyl)amino]-2-[(tert-butoxycarbonyl)amino]butanoate (0.66 g, 1.495 mmol), benzyl bromide (1.023 g, 5.98 mmol) and K2CO3 (0.620 g, 4.49 mmol) was added MeCN (15 ml) and DMF (1 ml). The suspension was heated overnight at 60° C. The reaction was then poured onto a mixture of water and EtOAc, the layers separated and the aqueous layer extracted with EtOAc. The combined organics were washed with water and brine, then dried (MgSO4), filtered and evaporated in vacuo to give an oil (˜1.5 g) which was subjected to column chromatography eluting with 5 to 10% EtOAc in hexanes to give the product (550 mg, 1.1 mmol, 69% yield). LCMS purity 95%: m/z 532 [M+H]+.

Workup

customthe layers separated
extractionthe aqueous layer extracted with EtOAc
washThe combined organics were washed with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-4e86b3d183b241639f210eb838ccf0cf
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106091B2

Reaction notes

Loading…