4-Methylmorpholine → N,N'-Dicyclohexylurea

HRID 1732603Notes

Reaction equation

HRID 1732603 reaction equation
CN1CC[O:5]CC1.[CH2:8]1[CH2:13][CH2:12][CH:11]([N:14]=[C:15]=[N:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:10][CH2:9]1.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[C:15]([NH:14][CH:11]1[CH2:10][CH2:9][CH2:8][CH2:13][CH2:12]1)([NH:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:5]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.05 ml of N-methylmorpholine and 100 mg of DCCI are added, at -5°, to a solution of 470 mg of Z-Asn-Phe-Phe-[D-Trp(F) -Lys(Boc)-Thr(But)-Phe-OH, 165 mg of H-Gaba-OBzl p-toluenesulphonate (Example 1.7A) and 66 mg of N-hydroxybenzotriazole in 2 ml of dimethylformamide. After 16 hours at this temperature, the reaction mixture is worked up analogously to Example 7.1. Except for traces of dicyclohexylurea, the product is obtained in the pure form.

Sources & evidence

ORD record
ord-aa22a7fc92764ac393cb75712cc2d055
Source dataset
uspto-grants-1980_12
Patent number
US04238481

Reaction notes

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