4-Chloroaniline → N-({4-Chloro[(4-ethoxyphenyl)sulfonyl]anilino}acetyl)valine

HRID 971324Notes

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.[Cl:33][C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1.[CH2:41]([O:43][C:44]1[CH:49]=[CH:48][C:47]([S:50](Cl)(=[O:52])=[O:51])=[CH:46][CH:45]=1)[CH3:42]>>[Cl:33][C:34]1[CH:40]=[CH:39][C:37]([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])[S:50]([C:47]2[CH:48]=[CH:49][C:44]([O:43][CH2:41][CH3:42])=[CH:45][CH:46]=2)(=[O:52])=[O:51])=[CH:36][CH:35]=1

Participants

Reactant 4

HCID 78124-Chloroaniline

HCID 60984Methyl bromoacetate

HCID 36883344-Ethoxybenzene-1-sulfonyl chloride

HCID 5164404Fmoc-N-methyl-DL-valine

Product 1

HCID 68615009N-({4-Chloro[(4-ethoxyphenyl)sulfonyl]anilino}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-chloroaniline and 4-ethoxybenzenesulfonyl chloride, the title compound was obtained in >60% purity by LC/MS. (ESI+): 483.

Sources & evidence

ORD record: ord-4b392c65fe234e3b9c4d25e6ee06d513
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312358B2

Reaction notes

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