1-Chloroethyl chloroformate → Carbamate

HRID 1167419Notes

Reaction equation

HRID 1167419 reaction equation
O1C=C[C:3](OC[C@@H]2[O:12][C:11](=[O:13])[N:10]([C:14]3C=[C:18](F)[C:17]([C:21]4CCNCC=4)=[C:16](F)[CH:15]=3)C2)=N1.Cl[C:29]([O:31][CH:32](Cl)[CH3:33])=[O:30]>ClCCl>[C:11](=[O:12])([O-:13])[NH2:10].[CH3:33][CH2:32][O:31][C:29]([CH3:3])=[O:30].[CH3:14][CH2:15][CH2:16][CH:17]([CH3:21])[CH3:18]

Participants

5

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 10136489HCID 10136489, compound

Product 2

HCID 276CarbamateHCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reference Example 5 (2.6 g, 5.57 mmol ) in dichloromethane (40 ml) was cooled, under an atmosphere of nitrogen, in an ice-water bath then 1-chloroethyl chloroformate (0.80 g, 5.59 mmol ) added dropwise via syringe. The resulting solution was stirred at ice temperature for 1 hour before isolating the intermediate product (carbamate) by flash chromatograhy (Merck 9385 silica, EtOAc/isohexane (1:1) eluant). The resulting gum was taken up in MeOH (40 ml) and refluxed for 1 hour. Evaporation of the solvent after this time gave the title product (1.46 g, 64%) as a crystalline solid.

Sources & evidence

ORD record
ord-7e50a778fcea407f9e98330ef70ea0ca
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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