Water → HCID 13772599, compound

HRID 986319Notes

Reaction equation

HRID 986319 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:16]1[CH:17]=[C:18]([CH:22]([CH3:43])[C:23]([NH:25][CH2:26][CH:27]([OH:42])[CH2:28][NH:29][C:30](=[O:41])[C@H:31]([CH3:40])[NH:32]C(OC(C)(C)C)=O)=[O:24])[CH:19]=[CH:20][CH:21]=1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>C(Cl)Cl.C(OCC)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:16]1[CH:17]=[C:18]([CH:22]([CH3:43])[C:23]([NH:25][CH2:26][CH:27]([OH:42])[CH2:28][NH:29][C:30](=[O:41])[C@H:31]([CH3:40])[NH2:32])=[O:24])[CH:19]=[CH:20][CH:21]=1)(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 13772595HCID 13772595, compound

Product 1

HCID 13772599HCID 13772599, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

While stirring at 0°, 6.4 ml (83.6 mmol) of trifluoroacetic acid (density=1.49) are added to a solution of 1.59 g (3.17 mmol) of N-tert.-butoxycarbonyl-L-alanine-3-[2-(3-benzoylphenyl)-propionylamino]-2-hydroxypropylamide, containing 0.21 mol of water, in 25 ml of absolute methylene chloride and the resulting solution is stirred for 3 hours at 0°. 60 ml of diethyl ether are then added to the clear colourless solution and the resulting suspension is stirred for 15 minutes at 0°. The colourless crystals formed are filtered off with suction and washed with diethyl ether. 1.45 g of crude product are obtained; this is suspended again in 50 ml of hot diethyl ether. After cooling, the suspension is stirred for a further one hour at room temperature and the resulting crystals are filtered off with suction and washed with diethyl ether. L-alanine-3-[2-(3-benzoylphenyl)-propionylamino]-2-hydroxypropylamide trifluoroacetate is obtained in the form of colourless crystals that decompose at 92° and above and contain 0.25 mol of water; [α]D20 =+10.9°±0.9° (c= 1.054; methylene chloride), Rf =0.12 (chloroform:methanol=4:1), Rf =0.17 (chloroform:methanol=7:3), Rf =0.23 (chloroform:methanol:water=70:30:5).

Workup

  1. stirringthe resulting suspension is stirred for 15 minutes at 0°
  2. customThe colourless crystals formed
  3. filtrationare filtered off with suction
  4. washwashed with diethyl ether
  5. custom1.45 g of crude product are obtained
  6. temperatureAfter cooling
  7. stirringthe suspension is stirred for a further one hour at room temperature
  8. filtrationthe resulting crystals are filtered off with suction
  9. washwashed with diethyl ether

Sources & evidence

ORD record
ord-7d0449bcf6db4b0fa00e961e8cb393b3
Source dataset
uspto-grants-1987_12
Patent number
US04711879

Reaction notes

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