Dicyclohexylcarbodiimide → HCID 54271067, compound

HRID 1659520Notes

Reaction equation

HRID 1659520 reaction equation
[C:1]1([O:7][C:8](=[O:22])[C@H:9]([CH2:18][CH2:19][S:20][CH3:21])[NH:10][C:11]([O:13]C(C)(C)C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ON1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2N=N1.C1CC[CH:36]([N:39]=C=NC2CCCCC2)CC1.[CH2:48](Cl)Cl.[CH3:51][N:52]([CH:54]=[O:55])C>>[C:1]1([O:7][C:8](=[O:22])[C@H:9]([CH2:18][CH2:19][S:20][CH3:21])[NH:10][C:11](=[O:13])[C@H:51]([CH2:48][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:52][C:54](=[O:55])[CH2:36][NH2:39])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 22350042dichloromethane N,N-dimethylformamideHCID 54357310HCID 54357310, compound

Product 1

HCID 54271067HCID 54271067, compound

Procedure

Starting from Boc-methionine phenyl ester resin (0.364 g, 0.15 m mol); glycyl-L-phenylalanyl-L-methionine phenyl ester resin was prepared as described in Example 1. After thorough washings, ##STR21## (47 mg, 0.095 m mol) in 1:1 CH2Cl2 /DMF (2 ml) containing 1-hydroxy benzotriazole (34 mg, 0.2 m mol) was treated with DCCI (0.15 m mol) and the mixture added to the resin and thoroughly stirred overnight. The resin was washed with DMF (3×), CH2Cl2 (3×), isopropanol (3×), CH2Cl2 (3×); 10% triethylamine in CH2Cl2 (2×), and CH2Cl2 (4×). Remaining amino groups were blocked by reaction with acetyl imidazole (0.2 g, 2 m mol) in DMF (5 ml) for 1 hour. The resin was thoroughly washed with DMF, CH2Cl2, isopropanol, CH2Cl2 and methanol. The dried resin weighed 0.413 g.

Workup

  1. additionthe mixture added to the resin and thoroughly stirred overnight
  2. washThe resin was washed with DMF (3×), CH2Cl2 (3×), isopropanol (3×), CH2Cl2 (3×)
  3. customRemaining amino groups were blocked by reaction with acetyl imidazole (0.2 g, 2 m mol) in DMF (5 ml) for 1 hour
  4. washThe resin was thoroughly washed with DMF, CH2Cl2, isopropanol, CH2Cl2 and methanol

Sources & evidence

ORD record
ord-f7bec6e2369443ba93004936fcc6ee97
Source dataset
uspto-grants-1981_12
Patent number
US04304715

Reaction notes

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