Triethylamine → Fmoc-Asp(Ot-Bu)-Trp-OBzl

HRID 985779Notes

Reaction equation

HRID 985779 reaction equation
[NH:1]([C:14]([O:16][CH2:17][CH:18]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[C@H:2]([C:11](O)=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].C1CCC(N=C=NC2CCCCC2)CC1.[NH2:46][C@H:47]([C:58]([O:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)=[O:59])[CH2:48][C:49]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[NH:51][CH:50]=1.Cl.C(N(CC)CC)C>C(Cl)Cl>[NH:1]([C:14]([O:16][CH2:17][CH:18]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[C@H:2]([C:11]([NH:46][C@H:47]([C:58]([O:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)=[O:59])[CH2:48][C:49]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[NH:51][CH:50]=1)=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2724635Fmoc-L-Asp(OtBu)-OHHCID 45073232L-tryptophan benzyl ester hydrochloride

Product 1

HCID 131722406Fmoc-Asp(Ot-Bu)-Trp-OBzl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 41 mg portion of Fmoc-Asp(Ot-Bu)-OH was dissolved in 1, ml of methylene chloride, and 12 mg of HONSu and 21 mg of DCC were added thereto at 0° C. and stirred at 0° C. for 30 minutes. Then, 1 ml of a methylene chloride solution containing 33 mg of H-Trp-OBzl hydrochloride and 14 μl of triethylamine were added thereto and stirred at 0° C. for 3 hours. The insoluble substances were removed by filtration and washed with cold methylene chloride, and the filtrate was collected. The solvent was removed from the filtrate by distillation under reduced pressure, and the residue was purified by silica gel column chromatography (50 g of Wakogel C-200, eluted with chloroform/methanol=25/1) to obtain 67 mg of Fmoc-Asp(Ot-Bu)-Trp-OBzl as a white powder.

Workup

  1. additionwere added
  2. additionwere added
  3. stirringstirred at 0° C. for 3 hours
  4. customThe insoluble substances were removed by filtration
  5. washwashed with cold methylene chloride
  6. customthe filtrate was collected
  7. customThe solvent was removed from the filtrate by distillation under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (50 g of Wakogel C-200, eluted with chloroform/methanol=25/1)

Sources & evidence

ORD record
ord-d4243957db784bfe8dcc63c1f1ed331a
Source dataset
uspto-grants-2005_03
Patent number
US06872803B1

Reaction notes

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