Hydrochloric Acid → HCID 178445915, compound

HRID 1607412Notes

Reaction equation

HRID 1607412 reaction equation
[C:1]1([CH2:11][CH:12]([CH2:37][CH2:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:13]([NH:15][C@H:16]([C:23]([NH:25][C@H:26](C=NNC(N)=O)[CH2:27][CH:28]([CH3:30])[CH3:29])=[O:24])[CH2:17][C:18]2[N:22]=[CH:21][NH:20][CH:19]=2)=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.C=O.[C:50](=[O:53])(O)[O-].[Na+]>CO>[C:1]1([CH2:11][CH:12]([CH2:37][CH2:38][CH2:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:13]([NH:15][C@H:16]([C:23]([NH:25][C@H:26]([CH:50]=[O:53])[CH2:27][CH:28]([CH3:29])[CH3:30])=[O:24])[CH2:17][C:18]2[N:22]=[CH:21][NH:20][CH:19]=2)=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 178445901HCID 178445901, compound

Product 1

HCID 178445915HCID 178445915, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.82 g of N-[2-(1-naphthylmethyl)-6-phenylhexanoyl]-L-histidyl-L-leucinal semicarbazone in 80 ml of methanol were added 29 ml of 1N-hydrochloric acid and 7.6 ml of a 37 wt% formaldehyde solution while ice-cooling under an argon atmosphere. The mixture was stirred for 1.5 hours at room temperature, and then a 5% aqueous sodium bicarbonate solution was added to the reaction mixture. The mixture was extracted with ethyl acetate, and the organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 1.55 g of N-[2-(1-naphthylmethyl)-6-phenylhexanoyl]-L-histidyl-L-leucinal as a white powder.

Workup

  1. temperaturecooling under an argon atmosphere
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2ff98dce0dad49338f81f68309e0abc4
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

Loading…