Acetate → Benzyloxycarbonylglycine

HRID 1416520Notes

Reaction equation

HRID 1416520 reaction equation
NCCOCCN.C([O-])(=O)C.C(=O)(O)[O-].[Na+].[CH2:17]([O:24][C:25]([NH:27][CH2:28][C:29]([O:31]C1C(F)=C(F)C(F)=C(F)C=1F)=[O:30])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O.O>[C:25]([NH:27][CH2:28][C:29]([OH:31])=[O:30])([O:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:26]

Participants

7

Reactant 4

HCID 175AcetateHCID 75982Bis(2-aminoethyl) etherHCID 516892Sodium BicarbonateHCID 10992405pentafluorophenyl N-benzyloxycarbonylglycinate

Product 1

HCID 14349BenzyloxycarbonylglycineYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The aminoethyl ether of Example 1 as the acetate (210 mg, 0.180 mmol) was dissolved in N,N-dimethylformamide (2 mL). To this solution 1M sodium bicarbonate (200 μL, 0.200 mmol) and pentafluorophenyl N-benzyloxycarbonylglycinate (106 mg, 0.270 mmol) were added. After 1 h, the reaction mixture was diluted with water (2×). Isolation by reverse-phase (C18) flash column chromatography eluting with 50-80% acetonitrile/water gave, after lyophilization of the product-containing fractions, the N-CBZ glycine conjugate of the above formula was obtained (130 mg):

Workup

  1. washIsolation by reverse-phase (C18) flash column chromatography eluting with 50-80% acetonitrile/water
  2. customgave

Sources & evidence

ORD record
ord-8d10e82f5d2c4173a3f4d967f7fefa07
Source dataset
uspto-grants-1999_06
Patent number
US05914313

Reaction notes

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