4-Nitrophenol → HCID 129844758, compound

HRID 1379596Notes

Reaction equation

HRID 1379596 reaction equation
[C:1](N[C@H](C(O)=O)C)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N[C@H](C(O)=[O:27])CC1C2C(=CC=CC=2)NC=1.[CH:29]1[C:34]([N+:35]([O-:37])=[O:36])=[CH:33]C=C(O)C=1.CN1CCOCC1.[I-:46].[I-].[Na+]>C(OC1(CCl)C=CC([N+]([O-])=O)=CC1)(=O)O>[C:1]([O:3][C:4]1([CH2:5][I:46])[CH:6]=[CH:29][C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH2:7]1)(=[O:2])[OH:27]

Participants

8

Reactant 6

HCID 9804-NitrophenolHCID 5238Sodium IodideHCID 6305L-TryptophanHCID 79724-MethylmorpholineHCID 30165Iodide IonHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 129844758HCID 129844758, compound

Reagents, catalysts & solvents 1

HCID 129844755HCID 129844755, compoundSolvent

Procedure

Scheme 5 shows the synthesis of compound 8, in which the promoiety is inserted in between Boc-alanine and a trytophan residue. This is achieved by first reacting 1-chloromethyl- chloroformate 2 with p-nitrophenol in the presence of N-methyl morpholine to yield 3. Substitution of chloride in 1-chloromethyl p-nitrophenol carbonate 3 with iodide is accomplished by reacting 3 with sodium iodide to give 1-iodomethyl p-nitrophenol carbonate (4) in quantitative yield. This iodo compound 4 is reacted with the cesium salt of Boc-alanine to yield Boc-alanineoxymethyl-p-nitrophenol carbonate 6.

Workup

  1. customto yield 3

Sources & evidence

ORD record
ord-84049cd3113b4a5cb408e1daa8d9292a
Source dataset
uspto-grants-1997_09
Patent number
US05672584

Reaction notes

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