1-Butanol → HCID 25114329, compound

HRID 2271387Notes

Reaction equation

HRID 2271387 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][C:15]=1[OH:16])[CH2:7][C@@H:8]([C:10]([OH:12])=[O:11])[NH2:9])([O-:3])=[O:2].[O:17](C(OC(C)(C)C)=O)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=O.C(O)CCC>[OH-].[Na+]>[C:18]([NH:9][C@H:8]([C:10]([OH:12])=[O:11])[CH2:7][C:6]1[CH:13]=[CH:14][C:15]([OH:16])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:17]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 651243-Nitro-L-tyrosineHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 25114329HCID 25114329, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.36 g (6.00 mmol) of 3-nitro-L-tyrosine in 30 mL of 1N NaOH, 1.74 g (8.00 mmol) of (BOC)2O in 8 mL of tent-butanol was added. The stiffing was continued overnight and the tert-butanol was removed in vacuo. Ethyl acetate (25 mL) was added to the residual aqueous layer and the resulting solution was cooled to 0° C. A solution of 1N KHSO4 was used to acidify the solution to pH 2 and the aqueous layer was separated and extracted with 25 mL of ethyl acetate (2×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to afford 0.265 g (13%) of the title compound as yellow solid.

Workup

  1. customthe tert-butanol was removed in vacuo
  2. additionEthyl acetate (25 mL) was added to the residual aqueous layer
  3. customthe aqueous layer was separated
  4. extractionextracted with 25 mL of ethyl acetate (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b8ec35c305742a0bdbe0fa43eb13c8e
Source dataset
uspto-grants-2015_09
Patent number
US09120744B2

Reaction notes

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