Hydrazine → HCID 145817244, compound

HRID 1384897Notes

Reaction equation

HRID 1384897 reaction equation
[CH:1]1[CH:6]=[N:5][C:4]2[N:7](O)[N:8]=N[C:3]=2[CH:2]=1.CCN(C(C)C)[CH:14]([CH3:16])[CH3:15].CC(OC([NH:27][C@@H:28]([C:35](O)=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=O)(C)C.NN>CN(C=O)C.C1COCC1.C(Cl)CCl>[C:29]1([C@H:28]([C:35]2[NH:8][N:7]=[C:4]([CH2:3][C:2]3[CH:16]=[CH:14][CH:15]=[CH:6][CH:1]=3)[N:5]=2)[NH2:27])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

8

Reactant 4

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 2755953(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid

Product 1

HCID 145817244HCID 145817244, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

EDC (1.6 g) was dissolved in DMF (20 ml.) and treated with HOAt (1.16 g) in DMF (10 ml.) and stirred for 10 mins. DIPEA (1.46 ml.) was then added and the stirring continued for a further 15 mins. Boc-D-phenylglycine (2 g) in DMF (10 ml.) was then added dropwise and stirring continued for a further 25 mins. 1M Hydrazine in THF (84 ml.) was then added and the mixture stirred over night. The solvents were then evaporated and the residue treated with water (100 ml.), basified with 2M sodium hydroxide solution and extracted with ethylacetate. The combined extracts were washed with water and brine, dried with magnesium sulphate, filtered and evaporated to give a yellow solid (1.38 g).

Workup

  1. waitthe stirring continued for a further 15 mins
  2. stirringstirring
  3. waitcontinued for a further 25 mins
  4. stirringthe mixture stirred over night
  5. customThe solvents were then evaporated
  6. additionthe residue treated with water (100 ml.)
  7. extractionextracted with ethylacetate
  8. washThe combined extracts were washed with water and brine
  9. dry with materialdried with magnesium sulphate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-23e94e1cf02f4a819e0f0b3ec42e1132
Source dataset
uspto-grants-2001_07
Patent number
US06262069B1

Reaction notes

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