Triethylamine → HCID 23002648, compound

HRID 398322Notes

Reaction equation

HRID 398322 reaction equation
[C:1]([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)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:22][CH:23]1[CH:27]=[CH:26][CH:25]([CH3:28])[NH:24]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.CCN(CC)CC>CN(C=O)C>[C:1]([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]([N:24]1[CH:25]([CH3:28])[CH:26]=[CH:27][CH:23]1[CH3:22])=[O:12])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1010662,5-Dimethyl-3-pyrrolineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 43933462-Tert-butoxycarbonylamino-3-(4-cyano-phenyl)-propionic acid

Product 1

HCID 23002648HCID 23002648, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.1 g of 2-[(N-Boc)amino]-3-(4-cyanophenyl)-propionic acid are mixed with 0.715 g of 2,5-dimethyl-2,5-dihydropyrrole in 10 ml of DMF, 3.9 g of BOP are added and the pH is adjusted to 7 by addition of Et3N. After stirring for 18 hours at RT, the mixture is evaporated to dryness and is then taken up in EtOAc, washed with NaHCO3 solution, with KHSO4/K2SO4 and with saturated NaCl solution. The resulting solution is dried over Na2SO4 and then evaporated. The residue is taken up in an ether/hexane mixture and then dried over Na2SO4. 1.4 g of the expected compound are obtained.

Workup

  1. additionare added
  2. customthe mixture is evaporated to dryness
  3. washwashed with NaHCO3 solution, with KHSO4/K2SO4 and with saturated NaCl solution
  4. dry with materialThe resulting solution is dried over Na2SO4
  5. customevaporated
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-d32f5079c35a48c898b27a2b4e1f31aa
Source dataset
uspto-grants-2003_08
Patent number
US06610882B2

Reaction notes

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