Triethylamine → HCID 54466648, compound

HRID 1576071Notes

Reaction equation

HRID 1576071 reaction equation
[C:1]([NH:4][C:5]1[CH:6]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])[S:7][CH2:8][C:9]=1[C:10]([OH:12])=O)(=[O:3])[CH3:2].C(N(CC)CC)C.Cl[C:33]([O:35][CH2:36][CH3:37])=[O:34]>CC(C)=O.O>[C:1]([NH:4][C:5]1[CH:6]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])[S:7][CH2:8][C:9]=1[C:10]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:12])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 54202553HCID 54202553, compound

Product 1

HCID 54466648HCID 54466648, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2.12 g (0.0060 moles) of 3-acetamido-4-carboxy-2,5-dihydro-2-thiophenevaleric acid piperidide was dissolved in 25 ml acetone to which 1.3 ml water had been added, and the solution was cooled in an ice bath for 15 min. At this point 1.8 ml (.0063 mole) of triethylamine was added in 25 ml acetone, followed immediately by the dropwise addition of 1.23 ml. (0.0063 mole) of ethyl chloroformate in 2.7 ml of acetone over a 10 minute period. The reaction was stirred at 0°C. for one hour to form 3-acetamido-4-carbethoxycarbonyl-2,5-dihydro-2-thiophenevaleric acid piperidide, which was converted to 3-(N-carbethoxyacetamido)-4-carboxy-2,5-dihydro-2-thiophenevaleric acid piperidide, and which was converted to 3-(N-carbethoxyacetamido)-4-carbethoxycarbonyl-2,5-dihydro-2-thiophenevaleric acid piperidide. A solution of 0.8 g. (0.0063 mole) sodium azide in 5 ml. water was added dropwise over a period of 5 minutes. The reaction was further stirred at 0° C. for 2 hrs. The reaction mixture was then partitioned between 100 ml. of dichloromethane and 75 ml. of ice water. The aqueous phase was extracted three times with anhydrous sodium sulfate to yield 2.8 g. (0.0060 mole, 100%) of 4-azidocarbonyl-3-(N-carbethoxyacetamido)-2,5-dihydro-2-thiophenevaleric acid piperidide as a colorless oil.

Workup

  1. additionhad been added
  2. temperaturethe solution was cooled in an ice bath for 15 min
  3. additionfollowed immediately by the dropwise addition of 1.23 ml

Sources & evidence

ORD record
ord-3c952b69bec74ee8b47db7daa95fb418
Source dataset
uspto-grants-1976_09
Patent number
US03979396

Reaction notes

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