Triethylamine → HCID 131723243, compound

HRID 2417156Notes

Reaction equation

HRID 2417156 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:23]1[CH2:34][CH2:33][CH2:32][C@@H:24]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C1C=CC2N(O)N=NC=2C=1.O.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(N(CC)CC)C>CN(C=O)C>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([N:23]1[CH2:34][CH2:33][CH2:32][C@@H:24]1[C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27960291-Hydroxybenzotriazole hydrateHCID 6931635H-D-Pro-otbu

Product 1

HCID 131723243HCID 131723243, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Z-L-Phe-OH (2.25 g, 7.5 mmol) and H-D-Pro-OtBu (0.862 g, 5.0 mmol) were dissolved in DMF (10 ml), mixed with HOBt H2O (766 mg, 5.0 mmol), BOP (3.3 g, 7.5 mmol) and triethylamine (1.75 ml, 12.5 mmol) under ice cooling, and then stirred for 2 hours. After the reaction mixture was concentrated, it was re-dissolved in ethyl acetate and washed sequentially with 10% citric acid, 4% NaHCO3 and brine. After drying over anhydrous MgSO4 and concentrating, the oily residue was purified by flash chromatography on silica gel (CHCl3/MeOH=99/1) to yield 1.403 g (62%) of the titled compound as an oil.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. dissolutionit was re-dissolved in ethyl acetate
  3. washwashed sequentially with 10% citric acid, 4% NaHCO3 and brine
  4. dry with materialAfter drying over anhydrous MgSO4
  5. concentrationconcentrating
  6. customthe oily residue was purified by flash chromatography on silica gel (CHCl3/MeOH=99/1)

Sources & evidence

ORD record
ord-b9e997739bce4340a3250db30feb90d2
Source dataset
uspto-grants-2004_11
Patent number
US06825317B2

Reaction notes

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