Sodium Carbonate → trans-3-amino-4-hydroxycyclopentene N-trichloroethyl urethane

HRID 1154962Notes

Reaction equation

HRID 1154962 reaction equation
[C:1]1([CH3:11])C(S(O)(=O)=O)=CC=CC=1.[NH2:12][C@H:13]1[C@H:17]([OH:18])[CH2:16][CH:15]=[CH:14]1.[C:19](=[O:22])([O-])[O-:20].[Na+].[Na+].[Cl:25][C:26]([Cl:33])([Cl:32])[CH2:27]OC(Cl)=O>O>[NH2:12][C@H:13]1[C@H:17]([OH:18])[CH2:16][CH:15]=[CH:14]1.[Cl:25][C:26]([Cl:33])([Cl:32])[CH2:27][NH:12][C:19]([O:20][CH2:1][CH3:11])=[O:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 86737601trans-3-Amino-4-hydroxycyclopentene toluenesulfonate

Product 1

HCID 70501488trans-3-amino-4-hydroxycyclopentene N-trichloroethyl urethane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 13.55 g. (50 mM) trans-3-amino-4-hydroxycyclopentene toluenesulfonate is dissolved in 75 ml. of water. The solution treated with 10.6 g. (10.0 mM) of sodium carbonate, cooled in an ice bath, and treated dropwise with 10.6 g. (50 mM) of trichloroethylchloroformate while stirring vigorously. After 75 min. the reaction is partitioned between water and methylene chloride. The aqueous layer is separated and extracted two times more with methylene chloride. The combined methylene chloride layer is dried over sodium sulfate and concentrated in vacuo. Crystals of trans-3-amino-4-hydroxy-cyclopentene-N-trichloroethyl urethane are formed during the concentration. These are collected three times, each time rinsing the crystals with ether crop 1, 6.12 g. m.p. 105.5°-106°; crop 2, 4.35 g., m.p. 105-106; crop 3, 1.28 g., m.p. 104°-105°.

Workup

  1. additionThe solution treated with 10.6 g
  2. additiontreated dropwise with 10.6 g
  3. customAfter 75 min. the reaction is partitioned between water and methylene chloride
  4. customThe aqueous layer is separated
  5. extractionextracted two times more with methylene chloride
  6. dry with materialThe combined methylene chloride layer is dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e72be5758e949e5a2910b3a867b3066
Source dataset
uspto-grants-1981_11
Patent number
US04298744

Reaction notes

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