Trifluoroacetic acid → HCID 23002643, compound

HRID 1870943Notes

Reaction equation

HRID 1870943 reaction equation
C([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=O)(OC(C)(C)C)=O.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:54]([OH:60])([C:56]([F:59])([F:58])[F:57])=[O:55]>CN(C=O)C.C(Cl)Cl.CCN(CC)CC>[F:57][C:56]([F:59])([F:58])[C:54]([OH:60])=[O:55].[NH2:8][CH:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=1)[C:10]([N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:12]

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 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 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4.06 g of 2-[N-(Boc)amino]-3-(4-cyanophenyl)propionic acid are mixed with 1.15 ml of pyrrolidine and 7.5 g of BOP in 20 ml of DMF; the mixture is left stirring for 2 hours at RT while maintaining at pH 7 by addition of Et3N. After evaporating to dryness, the residue is chromatographed on silica, eluting with a chloroform/methanol mixture (9/0.5; v/v). After evaporating off the solvents, the solid obtained is treated with 20 ml of TFA in 20 ml of DCM for 30 minutes at RT. The solvents are evaporated off and the residue is taken up in ether and then dried in order to obtain 3.95 g of the expected product.

Workup

  1. waitthe mixture is left
  2. customAfter evaporating to dryness
  3. customthe residue is chromatographed on silica
  4. washeluting with a chloroform/methanol mixture (9/0.5
  5. customAfter evaporating off the solvents
  6. customthe solid obtained
  7. customThe solvents are evaporated off
  8. customdried in order

Sources & evidence

ORD record
ord-f8fd004ccfc64d56a7f7e8969622148d
Source dataset
uspto-grants-2000_08
Patent number
US06100278

Reaction notes

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