Triethylamine → HCID 178517876, compound

HRID 1456344Notes

Reaction equation

HRID 1456344 reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][S:3]1.Cl.[O:11]([CH2:15][CH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][NH2:24])[CH2:19][CH2:18]1)[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.C1C=CC(OP(OC2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1>O1CCCC1>[O:11]([CH2:15][CH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][NH:24][C:7]([C@@H:5]2[CH2:4][S:3][C:2](=[O:1])[NH:6]2)=[O:9])[CH2:19][CH2:18]1)[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 72390ProcysteineHCID 123414Diphenylphosphoryl azideHCID 178479222HCID 178479222, compound

Product 1

HCID 178517876HCID 178517876, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 20 ml of anhydrous tetrahydrofuran was suspended 191 mg of (4R)-2-oxo-4-thiazolidinecarboxylic acid and 294 mg of trans-4-(2-nitroxyethyl)cyclohexylmethylamine hydrochloride, and 0.54 ml of triethylamine and 0.28 ml of diphenylphosphoric azide were added thereto with stirring under ice-cooling, and the resulting mixture was stirred at room temperature for 4 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluting solvent: cyclohexane/ethyl acetate=1/3) and recrystallizated from dichloromethane-diisopropyl ether to obtain 200 mg of the desired compound as a colorless crystalline solid.

Workup

  1. additionwere added
  2. temperaturecooling
  3. stirringthe resulting mixture was stirred at room temperature for 4 hours
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluting solvent: cyclohexane/ethyl acetate=1/3)

Sources & evidence

ORD record
ord-1e3631b6b0ab41ed88ccfcb437d8479f
Source dataset
uspto-grants-1998_12
Patent number
US05843973

Reaction notes

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