Trifluoroacetic acid → HCID 23002643, compound

HRID 1371536Notes

Reaction equation

HRID 1371536 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=N1.C(OC([NH:35][CH:36]([CH2:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[CH:43][CH:42]=1)[C:37]([OH:39])=O)=O)(C)(C)C.N1CCCC1.C(N1CCOCC1)C.[C:62]([OH:68])([C:64]([F:67])([F:66])[F:65])=[O:63]>CN(C=O)C.C(Cl)Cl>[F:65][C:64]([F:67])([F:66])[C:62]([OH:68])=[O:63].[NH2:35][CH:36]([CH2:40][C:41]1[CH:42]=[CH:43][C:44]([C:47]#[N:48])=[CH:45][CH:46]=1)[C:37]([N:10]1[CH2:11][CH2:16][CH2:15][CH2:14]1)=[O:39]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7525EthylmorpholineHCID 31268PyrrolidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 43933462-Tert-butoxycarbonylamino-3-(4-cyano-phenyl)-propionic acid

Product 1

HCID 23002643HCID 23002643, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

7.5 g of BOP are added to a mixture of 4.06 g of 2-(tert-butoxycarbonylamino)-3-(4-cyanophenyl)propionic acid and 1.15 ml of pyrrolidine in 20 ml of DMF, and the mixture is stirred for 2 hours at RT, while keeping the pH at 7 by adding N-ethylmorpholine. The reaction mixture is concentrated under vacuum and the residue is chromatographed on silica gel, eluting with a chloroform/MeOH mixture (95/5; v/v). The product obtained is taken up in 20 ml of TFA in 20 ml of DCM, and the reaction mixture is stirred for 30 minutes at RT and concentrated under vacuum. The residue is taken up in ether and the precipitate formed is filtered off by suction. 3.95 g of the expected product are obtained after drying.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. customthe residue is chromatographed on silica gel
  3. washeluting with a chloroform/MeOH mixture (95/5; v/v)
  4. customThe product obtained
  5. stirringthe reaction mixture is stirred for 30 minutes at RT
  6. concentrationconcentrated under vacuum
  7. customthe precipitate formed
  8. filtrationis filtered off by suction

Sources & evidence

ORD record
ord-da0a9db19de74e02886b0026c8a0cdb5
Source dataset
uspto-grants-2007_01
Patent number
US07157454B2

Reaction notes

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