Benzylamine → HCID 131711285, compound

HRID 1111719Notes

Reaction equation

HRID 1111719 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])[NH2:6].ON1C2C=CC=CC=2N=N1.[CH2:38](N)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C1CCC(N=C=NC2CCCCC2)CC1>O1CCCC1>[NH:1]([C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])[C@@H:2]([C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH:6][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 14420426HCID 14420426, compound

Product 1

HCID 131711285HCID 131711285, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 11.4 grams of Z-D-Gln-OBzl and 4.15 grams of 1-hydroxybenzotriazole in 50 ml of absolute tetrahydrofurane are added 3.35 ml of benzylamine and 6.76 grams of DCC. The mixture is stirred for 1 hour at 0° C and 1 hour at room temperature, the precipitate is filtered off with suction and the filtrate is concentrated. The residue is triturated in succession with NaHCO3 solution, 2n-HCl NaHCO3 solution and water, filtered off with suction and washed with water. Yield: 16.2 grams, melting point 144°. For purification recrystallisation from isopropanol is carried out. The product is washed with petroleum ether. Yield: 6 grams, melting point 149°, [α]D20 = -0.1 (c = 1, in glacial acetic acid.

Workup

  1. filtrationthe precipitate is filtered off with suction
  2. concentrationthe filtrate is concentrated
  3. customThe residue is triturated in succession with NaHCO3 solution, 2n-HCl NaHCO3 solution and water
  4. filtrationfiltered off with suction
  5. washwashed with water
  6. customFor purification recrystallisation from isopropanol
  7. washThe product is washed with petroleum ether

Sources & evidence

ORD record
ord-ac45eb1bc3084905bc6a6f441794f4bd
Source dataset
uspto-grants-1978_10
Patent number
US04118483

Reaction notes

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