Dicyclohexylcarbodiimide → Z-(L)-Val-(L)-Tyr morpholin-4-ylamide

HRID 263764Notes

Reaction equation

HRID 263764 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[NH:26]([C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])[C@H:27]([C:31]([OH:33])=O)[CH:28]([CH3:30])[CH3:29].[NH2:44][C@H:45]([C:54]([OH:56])=[O:55])[CH2:46][C:47]1[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=1.[N:57]1([NH-:63])[CH2:62][CH2:61][O:60][CH2:59][CH2:58]1>C(Cl)Cl>[NH:26]([C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])[C@H:27]([C:31]([NH:44][C@H:45]([C:54]([OH:56])=[O:55])[CH2:46][C:47]1[CH:48]=[CH:49][C:50]([OH:53])=[CH:51][CH:52]=1)=[O:33])[CH:28]([CH3:29])[CH3:30].[N:57]1([NH-:63])[CH2:62][CH2:61][O:60][CH2:59][CH2:58]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 726987N-Carbobenzoxy-L-valineHCID 131720081H-(L)-Tyr morpholin-4-ylamide

Product 1

HCID 131720082Z-(L)-Val-(L)-Tyr morpholin-4-ylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 0° C., 5.18 g (25 mmol) of DCC and 3.73 g (27.5 mmol) of HOBT are added to a solution of 6.3 g (25 mmol) of Z-(L)-Val-OH in 400 ml of methylene chloride and the mixture is then stirred for 20 min. A solution of 6.27 g (25 mmol) of H-(L)-Tyr-morpholin-4-ylamide in 600 ml of methylene chloride is subsequently added. After the mixture has been stirred for 18 h at RT, working up is carried out as described in Example 41 A) a): TLC Rf (B)=0.50.

Workup

  1. stirringAfter the mixture has been stirred for 18 h at RT

Sources & evidence

ORD record
ord-1ac7388b56fd44fea2de8288ad74013b
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

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