Dicyclohexylcarbodiimide → HCID 178447300, compound

HRID 1609193Notes

Reaction equation

HRID 1609193 reaction equation
[C:1]([C@@H:4]([N:8]([C:27](=[O:32])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]2[NH:26][N:25]=[N:24][N:23]=2)=[CH:12][CH:11]=1)[CH:5]([CH3:7])[CH3:6])(O)=[O:2].Cl.[NH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1.C(N(C(C)C)C(C)C)C.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[OH:43][C:40]1[CH:41]=[CH:42][C:37]([CH2:36][CH2:35][NH:34][C:1]([C@@H:4]([N:8]([C:27](=[O:32])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:23][N:24]=[N:25][N:26]=3)=[CH:12][CH:11]=2)[CH:5]([CH3:7])[CH3:6])=[O:2])=[CH:38][CH:39]=1

Participants

7

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 66449Tyramine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 178447302HCID 178447302, compound

Product 1

HCID 178447300HCID 178447300, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.5 g of the compound from Example 16, 0.21 g of tyramine hydrochloride, 0.225 ml of N-ethyldiisopropylamine, 0.164 g of 1-hydroxybenzotriazole and 0.296 g of dicyclohexylcarbodiimide are stirred at room temperature in 4 ml of DMF for 48 h. After evaporating the solvent in vacuo, the residue is stirred in a mixture of 4 ml of CH2Cl2 -MeOH-AcOH 94:3:3 for 1 h. After evaporating, the mixture is separated by means of flash chromatography (100 g, system N6). After lyophilizing from t-BuOH, the product is obtained as an amorphous powder. FAB-MS: m/e=555 (M+H)+.

Workup

  1. customAfter evaporating the solvent in vacuo
  2. customAfter evaporating
  3. customthe mixture is separated by means of flash chromatography (100 g, system N6)
  4. customthe product is obtained as an amorphous powder

Sources & evidence

ORD record
ord-07220b9b4b1143b2a5abd99648b0c1ba
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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