1,2-Dichloroethane → HCID 31808933, compound

HRID 879242Notes

Reaction equation

HRID 879242 reaction equation
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)C(C)C)(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[C:43]([NH:51][NH2:52])(=[O:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CN(C=O)C>[C:4]([O:3][C:1](=[O:2])[NH:8][C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]([NH:52][NH:51][C:43](=[O:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:19])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 11955BenzoylhydrazineHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 81531Diisopropylethylamine

Product 1

HCID 31808933HCID 31808933, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 mg (754 μmol) of N-Boc-L-phenylalanine were dissolved in 8 ml of DMF mixed with 131 μl (754 μmol) of N,N-diisopropylethylamine, 346 mg (2261 μmol) of HOBt, 434 mg (2261 μmol) of EDC, and 411 mg (3015 μmol) of benzoyl hydrazine. The reaction composition was stirred at RT overnight, then evaporated, and the residue purified over preparative HPLC. The yield was 313 mg (95% purity, 100% o. th.) of the title compound.

Workup

  1. customevaporated
  2. customthe residue purified over preparative HPLC

Sources & evidence

ORD record
ord-b76a583eb60547daa89e2019ebd7a41e
Source dataset
uspto-grants-2015_03
Patent number
US08987209B2

Reaction notes

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