Ethylmorpholine → HCID 22732134, compound

HRID 1371537Notes

Reaction equation

HRID 1371537 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:28]([O:32][C:33]([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:34])([CH3:31])([CH3:30])[CH3:29].N1CCCC1.C(N1CCOCC1)C>CN(C=O)C>[C:28]([O:32][C:33]([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]([N:10]1[CH2:11][CH2:16][CH2:15][CH2:14]1)=[O:39])=[O:34])([CH3:29])([CH3:30])[CH3:31]

Participants

6

Reactant 4

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

Product 1

HCID 22732134HCID 22732134, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 maintaining 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). 3.8 g of the expected product are obtained.

Workup

  1. temperaturewhile maintaining the pH at 7
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. customthe residue is chromatographed on silica gel
  4. washeluting with a chloroform/MeOH mixture (95/5; v/v)

Sources & evidence

ORD record
ord-6518015e35704478a6f810ca1037f544
Source dataset
uspto-grants-2007_01
Patent number
US07157454B2

Reaction notes

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