(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile → HCID 86739822, compound

HRID 1154416Notes

Reaction equation

HRID 1154416 reaction equation
[CH3:1][C:2]1([CH3:18])[C@@H:4](/[CH:5]=[C:6](\[Br:14])/[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C@H:3]1[C:15]([OH:17])=[O:16].[C:19]([C@@H:21](O)[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:23]=1)#[N:20]>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:18])[C@@H:4](/[CH:5]=[C:6](\[Br:14])/[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C@H:3]1[C:15]([O:17][C@H:21]([C:19]#[N:20])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:23]=1)=[O:16]

Participants

4

Reactant 2

HCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 86739823HCID 86739823, compound

Product 1

HCID 86739822HCID 86739822, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the process of Example 1, (1R,cis) 2,2-dimethyl-3(Z)-[2-bromo-3-oxo-3-tert.-butoxy-propenyl]-cyclopropane-1-carboxylic acid and (S)α-cyano-3-phenoxy-benzyl alcohol were reacted to obtain (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3(Z)-[2-bromo-3-oxo-3-tert.-butoxy-propenyl]-cyclopropane-1-carboxylate with a specific rotation of [α]D20 =+16.5°±2° (c=0.5% in chloroform).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-fcb66ab7eaed4ba2bf9acc5521e285fa
Source dataset
uspto-grants-1984_12
Patent number
US04489093

Reaction notes

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