Nitrogen → HCID 23456069, compound

HRID 2065012Notes

Reaction equation

HRID 2065012 reaction equation
N#N.[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]([OH:14])=O)=[O:9])([CH3:6])([CH3:5])[CH3:4].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH3:40][O:41][C:42](=[O:53])[CH:43]([NH2:52])[CH:44]([OH:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(Cl)Cl.OS([O-])(=O)=O.[K+]>[CH3:40][O:41][C:42](=[O:53])[CH:43]([NH:52][C:12](=[O:14])[CH2:11][NH:10][C:8]([O:7][C:3]([CH3:4])([CH3:5])[CH3:6])=[O:9])[CH:44]([OH:51])[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

8

Reactant 5

HCID 947NitrogenHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 3639766HCID 3639766, compound

Product 1

HCID 23456069HCID 23456069, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516920Potassium bisulfateSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of tert-butoxycarbonylamino-acetic acid (906 mg, 5.12 mmol) in CH2Cl2 (27.0 mL) was treated at 0° C. with HOBt (777 mg, 5.64 mmol), DCC (1.17 g, 5.64 mmol) N-methylmorpholine (0.85 mL, 7.68 mmol) and 2-amino-3-hydroxy-3-phenyl-propionic acid methyl ester (1.00 g, 5.12 mmol). The resulting mixture was stirred at rt for 2 h, poured in 5% KHSO4 (100 mL), stirred for 15 min, filtered and washed with CH2Cl2. The aqueous phase was extracted with CH2Cl2 and the combined organic phases were washed with sat. aq. NaHCO3, brine, dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC(CH2Cl2 to 99:1 CH2Cl2-MeOH) gave the title compound as a white solid. TLC: rf (90:10 CH2Cl2-MeOH)=0.48. LC-MS-conditions 02: tR=0.85 min, [M+H]+=353.05.

Workup

  1. stirringstirred for 15 min
  2. filtrationfiltered
  3. washwashed with CH2Cl2
  4. extractionThe aqueous phase was extracted with CH2Cl2
  5. washthe combined organic phases were washed with sat. aq. NaHCO3, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customPurification of the residue by FC(CH2Cl2 to 99:1 CH2Cl2-MeOH)

Sources & evidence

ORD record
ord-4e96f9df3f7e4a49aea7297332a97d41
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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