Ethyl bromodifluoroacetate → 1-Naphthaleneacetic acid, 7-bromo-1-[[(R)-(1,1-dimethylethyl)sulfinyl]amino]-α,α,4,4-tetrafluoro-1,2,3,4-tetrahydro-, ethyl ester, (1R)-

HRID 1525147Notes

Reaction equation

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

Participants

Reactant 2

HCID 69585Ethyl bromodifluoroacetate

HCID 89253730HCID 89253730, compound

Product 1

HCID 710596711-Naphthaleneacetic acid, 7-bromo-1-[[(R)-(1,1-dimethylethyl)sulfinyl]amino]-α,α,4,4-tetrafluoro-1,2,3,4-tetrahydro-, ethyl ester, (1R)-Yield 58%

Procedure

Starting from (R)-2-methyl-propane-2-sulfinic acid [7-bromo-4,4-difluoro-3,4-dihydro-2H-naphthalen-(1E)-ylidene]-amide (intermediate A2.4) and ethyl 2-bromo-2,2-difluoroacetate, the product [(R)-7-bromo-4,4-difluoro-1-((R)-2-methyl-propane-2-sulfinylamino)-1,2,3,4-tetrahydro-naphthalen-1-yl]-difluoro-acetic acid ethyl ester (58% yield) was obtained as a brown solid. MS (ISP): m/z=488.1 [M+H]+ and 490.0 [M+H]+.

Sources & evidence

ORD record: ord-a4419e841ab0493cb078ab0308f78a18
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079919B2

Reaction notes

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