Acetic Acid Mixture with Hydrobromic Acid → HCID 178419252, compound

HRID 464904Notes

Reaction equation

HRID 464904 reaction equation
C(OC([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36][C@H:37]([CH2:42][OH:43])[CH2:38][CH:39]([CH3:41])[CH3:40])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=O)C1C=CC=CC=1.[BrH:44].C(O)(=O)C>C(OCC)C>[BrH:44].[BrH:44].[C:14]1([CH2:13][C@@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36][C@H:37]([CH2:42][OH:43])[CH2:38][CH:39]([CH3:40])[CH3:41])=[O:35])[CH2:28][C:29]2[N:33]=[CH:32][NH:31][CH:30]=2)=[O:25])[NH2:11])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 178445919HCID 178445919, compound

Product 1

HCID 178419252HCID 178419252, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 0.59 g. (1 mmole) of N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-L-histidyl-L-leucinol (prepared as described in Example 9) were added 10 ml. of a 25% w/v hydrogen bromide/acetic acid solution. The mixture was stirred at room temperature for 30 minutes, after which there were added 100 ml. of anhydrous diethyl ether. The white precipitate thus formed was separated by filtration, thoroughly washed with diethyl ether and dried in a desiccator. There was obtained 0.52 g. of the desired compound as a white powdery solid, melting at 155°-159° C.; [α]24 +21.0° (C=0.5, methanol).

Workup

  1. additionafter which there were added 100 ml
  2. customThe white precipitate thus formed
  3. customwas separated by filtration
  4. washthoroughly washed with diethyl ether
  5. customdried in a desiccator
  6. customThere was obtained 0.52 g

Sources & evidence

ORD record
ord-e7b32670687740748fb0a97c4e194740
Source dataset
uspto-grants-1985_10
Patent number
US04548926

Reaction notes

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