Hydrogen Bromide → HCID 131712420, compound

HRID 1578159Notes

Reaction equation

HRID 1578159 reaction equation
[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH2:4][CH2:5][CH3:6].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[NH2:35][C@H:36]([C:41]([NH:43][C@H:44]([C:52]([NH:54][C@H:55]([C:63]([O:65][CH3:66])=[O:64])[CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[O:53])[CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:42])[CH2:37][C:38](=[O:40])[NH2:39].Br>O1CCCC1.CN(C)C=O.O1CCCC1.C(O)C>[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C@H:2]([C:7]([NH:35][C@H:36]([C:41]([NH:43][C@H:44]([C:52]([NH:54][C@H:55]([C:63]([O:65][CH3:66])=[O:64])[CH2:56][C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)=[O:53])[CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:42])[CH2:37][C:38](=[O:40])[NH2:39])=[O:9])[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

9

Reactant 5

HCID 260Hydrogen BromideHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 6993403Z-Nle-OHHCID 25797686HCID 25797686, compound

Product 1

HCID 131712420HCID 131712420, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

4.95 g of Z-Nle-OH dissolved in 50 ml tetrahydrofuran are cooled to -20° C. and 2.1 ml of N-methylmorpholine followed by 2.43 ml of chloroformic acid isobutylester are added to the solution with stirring. The solution is stirred for a further 10 minutes at -15° C. and a cold solution comprising 10.6 g of H-Asn-Phe-Phe-OMe. hydrobromide and 2.5 ml of N-methylmorpholine in 60 ml N,N-dimethylformamide/tetrahydrofuran (1:1) are added. The solution is stirred for 20 hours at 0° C. and for 2 hours at room temperature and subsequently stirred with aqueous ethanol. After filtration, washing with (a) methanol and (b) ether and drying, the title compound is obtained [α]D20 =-31° (c=1.0 in dimethylformamide): decomposition at 235° C.

Workup

  1. additionare added to the solution
  2. stirringThe solution is stirred for a further 10 minutes at -15° C.
  3. stirringThe solution is stirred for 20 hours at 0° C. and for 2 hours at room temperature
  4. filtrationAfter filtration
  5. washwashing with (a) methanol and (b) ether
  6. customdrying

Sources & evidence

ORD record
ord-b9170776db75435b8a04a385a26ffea8
Source dataset
uspto-grants-1981_09
Patent number
US04291022

Reaction notes

Loading…