Triethylamine hydrochloride → HCID 178501433, compound

HRID 1600376Notes

Reaction equation

HRID 1600376 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH2:17][C:18]#[N:19])[C:13]([O-:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:20]=[N+:21]=[N-:22].Cl.[CH2:24](N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH2:17][C:18]1[NH:22][N:21]=[N:20][N:19]=1)[C:13]([O:15][CH3:24])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33558AzideHCID 86752494(2S)-2-benzyloxycarbonylamino-4-cyanobutyrate

Product 1

HCID 178501433HCID 178501433, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into the same device as used in Example 1 were placed 77.3 g (0.28 mole) ofmethyl (2S)-2-benzyloxycarbonylamino-4-cyanobutyrate, 27.3 g (0.42 mole) ofsodium azide, 57.7 g (0.42 mole) of triethylamine hydrochloride and 280 ml of toluene. Thereafter, the mixture was heated to a temperature of 82° to 83° C. to undergo a reaction for 24 hours. Subsequently the same procedure as in Example 1 was repeated, and crystalswere collected by filtration. Further, the crystals were recrystallized from methanol and water, filtered and dried, giving 67.7 g (0.21 mole) of methyl (2S)-2-benzyloxycarbonylamino-4-(tetrazole-5-yl)butyrate (yield 75.8% based on methyl (2S)-2-benzyloxycarbonylamino-4-cyanobutyrate). The reaction is illustrated below with chemical formulas: ##STR27##

Workup

  1. temperatureThereafter, the mixture was heated to a temperature of 82° to 83° C.
  2. customa reaction for 24 hours
  3. filtrationcrystalswere collected by filtration
  4. customFurther, the crystals were recrystallized from methanol and water
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-fc3bcc8ab7bb4d70bd1ed0cd3bc5c1a2
Source dataset
uspto-grants-1998_04
Patent number
US05744612

Reaction notes

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