Sulfuric Acid → HCID 131717738, compound

HRID 2081545Notes

Reaction equation

HRID 2081545 reaction equation
[NH2:1][C@:2]([C:6]([NH:8][C@H:9]([C:17]([NH:19][C@H:20]([C:24]([NH:26][C@H:27]([C:35](O)=[O:36])[CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)=[O:25])[CH2:21][CH2:22][CH3:23])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH2:4][CH3:5])[CH3:3].C[N-]OC.[H-].[H-].[H-].[H-].[Li+].[Al+3].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].S(=O)(=O)(O)O>C1COCC1.CC(=O)OCC>[NH2:1][C@:2]([C:6]([NH:8][C@H:9]([C:17]([NH:19][C@H:20]([C:24]([NH:26][C@H:27]([CH:35]=[O:36])[CH2:28][CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1)=[O:25])[CH2:21][CH2:22][CH3:23])=[O:18])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH2:4][CH3:5])[CH3:3]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydride2×HCID 131717739HCID 131717739, compound

Product 1

HCID 131717738HCID 131717738, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 640 mg (1.18 mmol) of Iva-Phe-Nva-Cha-N,O-dimethylhydroxylamide in 3.2 ml of absolute THF is added dropwise to a suspension of 60.8 mg (1.59 mmol) of LAH in 1.6 ml of absolute THF at -5° C.; after 2.5 hours at 0° C., a further 30.5 mg (0.8 mmol) of LAH are added, and the mixture is stirred at 0° C. for a further 30 minutes, cooled to -10° C. and 1.08 ml of saturated Seignette salt solution is slowly added dropwise, and the mixture is stirred for 30 minutes and then 2.46 ml of 2N sulfuric acid are added dropwise. EA is poured onto the reaction mixture, which is stirred for 30 minutes, the solution is decanted off from the precipitate, and the residue is extracted twice with EA. The combined organic phases are washed with water, saturated sodium bicarbonate solution and saturated sodium chloride solution, dried and concentrated at R.T. 470 mg of the title compound are obtained and rapidly reacted further.

Workup

  1. temperaturecooled to -10° C.
  2. stirringthe mixture is stirred for 30 minutes
  3. stirringis stirred for 30 minutes
  4. customthe solution is decanted off from the precipitate
  5. extractionthe residue is extracted twice with EA
  6. washThe combined organic phases are washed with water, saturated sodium bicarbonate solution and saturated sodium chloride solution
  7. customdried
  8. concentrationconcentrated at R.T

Sources & evidence

ORD record
ord-b103a32ccaa744c8b0d6026d20b033cc
Source dataset
uspto-grants-1993_02
Patent number
US05185324

Reaction notes

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