Triethylamine → N-(Benzyloxycarbonyl)-4,6-dibromotryptophan ethyl ester

HRID 2379120Notes

Reaction equation

HRID 2379120 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([Br:18])=[CH:14][C:15]=2[Br:17])[NH:10][CH:9]=1)[NH2:6])[CH3:2].C(N(CC)CC)C.Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([Br:18])=[CH:14][C:15]=2[Br:17])[NH:10][CH:9]=1)[NH:6][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 186560674,6-Dibromotryptophan ethyl ester

Product 1

HCID 53945469N-(Benzyloxycarbonyl)-4,6-dibromotryptophan ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Mix DL-4,6-dibromotryptophan ethyl ester (1.20g, 3.07mmol), triethylamine (341mg, 3.38mmol)and methylene chloride (50mL). Add benzyl chloroformate (692mg, 4.06mmol) and stir for 12 hours. Dilute with methylene chloride, wash with 1M hydrochloric acid (100mL) and brine (100mL). Dry (MgSO4) and evaporate the solvent in vacuo and purify by silica gel chromatography to give the title compound.

Workup

  1. washwash with 1M hydrochloric acid (100mL) and brine (100mL)
  2. dry with materialDry (MgSO4)
  3. customevaporate the solvent in vacuo
  4. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-a024dcab52fc4279a4cbfe105bd69594
Source dataset
uspto-grants-1994_11
Patent number
US05360814

Reaction notes

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