Tert-Butylamine → Z-D-Gln(But)-OBzl

HRID 1111721Notes

Reaction equation

HRID 1111721 reaction equation
[NH:1]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@@H:2]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])O.ON1C2C=CC=CC=2N=N1.[C:38]([NH2:42])([CH3:41])([CH3:40])[CH3:39].C1CCC(N=C=NC2CCCCC2)CC1>O1CCCC1>[NH:1]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@@H:2]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH:42][C:38]([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7018162Z-D-Glu-OBzl

Product 1

HCID 131711287Z-D-Gln(But)-OBzl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 9.9 grams of Z-D-Glu-OBzl and 3.6 grams of 1-hydroxybenzotriazole in 50 ml of absolute tetrahydrofurane are added 1.96 grams of tert.-butylamine and at 0° C. 5.86 grams of DCC. The mixture is stirred for 2 hours at 0° C. and overnight at room temperature. The next day the precipitate is filtered off with suction and the filtrate is concentrated. The residue is dissolved in ethyl acetate and the solution is washed in succession with a saturated solution of sodium bicarbonate, 2n-HCl, a saturated solution of sodium bicarbonate and water, dried with sodium sulphate and concentrated. Yield: 4.6 gams of an oil.

Workup

  1. customat 0° C
  2. filtrationThe next day the precipitate is filtered off with suction
  3. concentrationthe filtrate is concentrated
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washthe solution is washed in succession with a saturated solution of sodium bicarbonate, 2n-HCl
  6. dry with materiala saturated solution of sodium bicarbonate and water, dried with sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fbc16a68ecfe42c7b4df584c20e83903
Source dataset
uspto-grants-1978_10
Patent number
US04118483

Reaction notes

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