Hydrogen Bromide → HCID 178445921, compound

HRID 464899Notes

Reaction equation

HRID 464899 reaction equation
C(OC([NH:11][C@H:12]([C:20]([NH:22][C@H:23]([C:30]([NH:32][C@H:33]([CH2:38][OH:39])[CH2:34][CH:35]([CH3:37])[CH3:36])=[O:31])[CH2:24][C:25]1[N:29]=[CH:28][NH:27][CH:26]=1)=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)C1C=CC=CC=1.Br.[N+:41]([C:44]1[C:45]([S:50][S:51][CH2:52][CH2:53][C:54]([OH:56])=O)=[N:46][CH:47]=[CH:48][CH:49]=1)([O-:43])=[O:42].ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>C(OCC)C.C(O)(=O)C>[N+:41]([C:44]1[C:45]([S:50][S:51][CH2:52][CH2:53][C:54]([NH:11][C@H:12]([C:20]([NH:22][C@H:23]([C:30]([NH:32][C@H:33]([CH2:38][OH:39])[CH2:34][CH:35]([CH3:36])[CH3:37])=[O:31])[CH2:24][C:25]2[N:29]=[CH:28][NH:27][CH:26]=2)=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:56])=[N:46][CH:47]=[CH:48][CH:49]=1)([O-:43])=[O:42]

Participants

8

Reactant 5

HCID 260Hydrogen BromideHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 20262176HCID 20262176, compoundHCID 178445922HCID 178445922, compound

Product 1

HCID 178445921HCID 178445921, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To 0.16 g. (0.3 mmole) of N-benzyloxycarbonyl-L-phenylalanyl-L-histidyl-L-leucinol were added 3 ml. of a 25% w/v glacial acetic acid solution of hydrogen bromide. The mixture was stirred at room temperature for 30 minutes, and then anhydrous diethyl ether was added thereto. The precipitate thus formed was separated by filtration and dissolved in 5 ml. of dimethylformamide. The solution was cooled with ice, and then there were added 30 mg. of N-methylmorpholine for neutralization. To the neutralized solution were added an active ester prepared from 86 mg. (0.33 mmole) of 3-(3-nitro-2-pyridyldithio)propionic acid, 39 mg. (0.33 mmole) of 1-hydroxybenztriazole and 74 mg. (0.36 mmole) of DCC. The mixture was stirred for 1 hour whilst cooling with ice and then overnight at room temperature, after which it was treated in a conventional manner to give a yellow powder, which was purified by silica gel column chromatography (eluent: chloroform/methanol=8:1 by volume), to afford 47 mg. of the desired compound as a yellow powdery solid, melting at 109°-112° C.; [α]22 -33.8° (C=0.5, methanol).

Workup

  1. customThe precipitate thus formed
  2. customwas separated by filtration
  3. dissolutiondissolved in 5 ml
  4. temperatureThe solution was cooled with ice
  5. additionthere were added 30 mg
  6. additionTo the neutralized solution were added an active ester
  7. customprepared from 86 mg
  8. stirringThe mixture was stirred for 1 hour
  9. temperaturewhilst cooling with ice
  10. additionovernight at room temperature, after which it was treated in a conventional manner
  11. customto give a yellow powder, which
  12. customwas purified by silica gel column chromatography (eluent: chloroform/methanol=8:1 by volume)
  13. customto afford 47 mg

Sources & evidence

ORD record
ord-82d6698c49bd4ee3803a07b1c317395d
Source dataset
uspto-grants-1985_10
Patent number
US04548926

Reaction notes

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