Ethylmorpholine → FMOC-N-Me-Ser(O-Bzl)-Tyr-D-Leu-OEt

HRID 1463651Notes

Reaction equation

HRID 1463651 reaction equation
[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl.C(N1CCOCC1)C.[N:33]([C:48]([O:50][CH2:51][CH:52]1[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[C:58]2[C:53]1=[CH:54][CH:55]=[CH:56][CH:57]=2)=[O:49])([CH3:47])[C@H:34]([C:44](O)=[O:45])[CH2:35][O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[N:33]([C:48]([O:50][CH2:51][CH:52]1[C:53]2[C:58](=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:59]2[C:64]1=[CH:63][CH:62]=[CH:61][CH:60]=2)=[O:49])([CH3:47])[C@H:34]([C:44]([NH:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:45])[CH2:35][O:36][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 44593820Fmoc-MeSer(Bzl)-OHHCID 131717344Tyr-D-Leu-OEt hydrochloride

Product 1

HCID 131717343FMOC-N-Me-Ser(O-Bzl)-Tyr-D-Leu-OEt

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent5×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of Tyr-D-Leu-OEt hydrochloride (1.649 g) in DMF (10 ml) cooled to 0° C. was added N ethylmorpholine (0.59 ml) in DMF (1 ml), followed by a solution of FMOC-N-Me-Ser(O-Bzl)-OH (2.18 g) in DMF (5 ml), followed by a solution of HOBt (0.9315 g) in DMF (5 ml), and followed by a solution of DCC (0.947 g) in DMF (2 ml). The reaction solution was stirred at 0° C. for 1 hour and then at room temperature for 4 hours. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography eluting with (95:5) methylene chloride:methanol. The product was obtained as a semisolid. Rf 0.35. Fab Mass spec. m/e 736 (M+ +H).

Workup

  1. waitat room temperature for 4 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by silica gel column chromatography
  4. washeluting with (95:5) methylene chloride
  5. customThe product was obtained as a semisolid

Sources & evidence

ORD record
ord-43351795ee2b4765b9e2d636edf3db5b
Source dataset
uspto-grants-1994_04
Patent number
US05300492

Reaction notes

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