N-(9-Fluorenylmethoxycarbonyloxy)succinimide → HCID 15295906, compound

HRID 2230276Notes

Reaction equation

HRID 2230276 reaction equation
[C:1]([O:5][C:6](=[O:17])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:18](ON1C(=O)CCC1=O)([O:20][CH2:21][CH:22]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19]>O1CCOCC1.O>[C:1]([O:5][C:6](=[O:17])[C@@H:7]([NH:8][C:18]([O:20][CH2:21][CH:22]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=2[C:29]2[C:34]1=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 6950582L-Tyrosine 1,1-dimethylethyl ester

Product 1

HCID 15295906HCID 15295906, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of -tyrosine t-butyl ester (Bachem, 20.0 g, 84.3 mmol) and FMOC-OSu (Bachem, 24.68 g, 71.2 mmol) was dissolved in 400 mL of dioxane and 400 mL of water. The pH of the resulting solution was adjusted to pH=9 and the solution stirred overnight at room temperature. The reaction mixture was concentrated to ½ volume and treated with concentrated HCl until the pH=5. The resulting solution was extracted with ethyl acetate (5×150 mL), the combined organic extracts were dried with MgSO4 and concentrated. The residue was crystallized from hot heptane/EtOAc. The solid that formed was collected by filtration and air dried to give the title compound (28.5 g, 87%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiontreated with concentrated HCl until the pH=5
  3. extractionThe resulting solution was extracted with ethyl acetate (5×150 mL)
  4. dry with materialthe combined organic extracts were dried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was crystallized from hot heptane/EtOAc
  7. customThe solid that formed
  8. filtrationwas collected by filtration and air
  9. customdried

Sources & evidence

ORD record
ord-9b8cfb860ff1454ea9ace16453e0b9ae
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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