Hydrochloric Acid → Z-Sta-Ala-Sta-OMe

HRID 1982324Notes

Reaction equation

HRID 1982324 reaction equation
[NH2:1][C@H:2]([C@H:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl.[NH:15]([C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[C@H:16]([C@H:21]([CH2:23][C:24]([NH:26][C@H:27]([C:29](O)=[O:30])[CH3:28])=[O:25])[OH:22])[CH2:17][CH:18]([CH3:20])[CH3:19].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C1CCC(N=C=NC2CCCCC2)CC1>O>[NH:15]([C:32]([O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:33])[C@H:16]([C@H:21]([CH2:23][C:24]([NH:26][C@H:27]([C:29]([NH:1][C@H:2]([C@H:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:30])[CH3:28])=[O:25])[OH:22])[CH2:17][CH:18]([CH3:20])[CH3:19]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 13384495H-Sta-OMeHCID 131714737Z-Sta-Ala-OH

Product 1

HCID 131714738Z-Sta-Ala-Sta-OMe

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a manner analogous to that described in stage 13.1, using as starting materials 150 mg of H-Sta-OMe×HCl (from stage 13.4), 253 mg of Z-Sta-Ala-OH (from stage 13.2), 102 mg of HOBt×H2O, 67 mg of N-methylmorpholine and 178 mg of DCCI, Z-Sta-Ala-Sta-OMe is obtained; Rf (chloroform/methanol ]9:1])=0.37.

Sources & evidence

ORD record
ord-67a045b688a746b0897f76661b8b4945
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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