Dicyclohexylcarbodiimide → Benzyl (tert-butoxycarbonyl)glycylglycinate

HRID 1655847Notes

Reaction equation

HRID 1655847 reaction equation
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=O.[NH2:13][CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([NH:13][CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[O:5]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 409140Benzyl glycinate

Product 1

HCID 3244524Benzyl (tert-butoxycarbonyl)glycylglycinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 10-20% excess of BOC-Gly-OH is coupled to the H-Gly-O-Bzl with DCC in dichloromethane for one hour. The solution is filtered and the solvent is removed on a rotary evaporator. The residue is taken up in ethyl acetate and washed successively with 1M KHSO4, water, saturated NaHCO3 solution, and water. The ethyl acetate solution is dried over MgSO4, filtered, and the solvent is removed on a rotary evaporator to form BOC-Gly-Gly-O-Bzl as a semisolid oil.

Workup

  1. filtrationThe solution is filtered
  2. customthe solvent is removed on a rotary evaporator
  3. washwashed successively with 1M KHSO4, water, saturated NaHCO3 solution, and water
  4. dry with materialThe ethyl acetate solution is dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed on a rotary evaporator

Sources & evidence

ORD record
ord-01c2877cc5234d79a3321f944ac57664
Source dataset
uspto-grants-1993_10
Patent number
US05252559

Reaction notes

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