4-Fluoroaniline → N-({[(3,4-Dimethoxyphenyl)sulfonyl]-4-fluoroanilino}acetyl)valine

HRID 971325Notes

Reaction equation

[C:1]([N:18](C)[CH:19]([CH:23]([CH3:25])[CH3:24])[C:20]([OH:22])=[O:21])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=[O:2].Br[CH2:28]C(OC)=O.[F:33][C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1.[CH3:41][O:42][C:43]1[CH:44]=[C:45]([S:51](Cl)(=[O:53])=[O:52])[CH:46]=[CH:47][C:48]=1[O:49][CH3:50]>>[CH3:41][O:42][C:43]1[CH:44]=[C:45]([S:51]([N:38]([CH2:28][C:1]([NH:18][C@H:19]([C:20]([OH:22])=[O:21])[CH:23]([CH3:25])[CH3:24])=[O:2])[C:37]2[CH:39]=[CH:40][C:34]([F:33])=[CH:35][CH:36]=2)(=[O:53])=[O:52])[CH:46]=[CH:47][C:48]=1[O:49][CH3:50]

Participants

Reactant 4

HCID 97314-Fluoroaniline

HCID 60984Methyl bromoacetate

HCID 27341833,4-Dimethoxybenzenesulfonyl chloride

HCID 5164404Fmoc-N-methyl-DL-valine

Product 1

HCID 68614109N-({[(3,4-Dimethoxyphenyl)sulfonyl]-4-fluoroanilino}acetyl)valine

Procedure

Following the general method as outlined in Example 75, starting from N-fmoc-3-methyl-2-methylamino-butyric acid, methyl bromoacetate, 4-fluoroaniline and 3,4-dimethoxybenzenesulfonyl chloride, the title compound was obtained in >60% purity by LC/MS. (ESI+): 483.

Sources & evidence

ORD record: ord-849b9a9290564240a2825ddaf8e03dab
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312358B2

Reaction notes

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