Phenyl chloroformate → Phenyl 4-(1,2,3-trihydroxypropan-2-yl)phenylcarbamate

HRID 1842979Notes

Reaction equation

HRID 1842979 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:13])([CH2:11][OH:12])[CH2:9][OH:10])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]>C1COCC1.O>[OH:10][CH2:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:20](=[O:21])[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:7][CH:6]=1)([OH:13])[CH2:11][OH:12]

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 866721652-(4-Aminophenyl)propane-1,2,3-triol

Product 1

HCID 86672166Phenyl 4-(1,2,3-trihydroxypropan-2-yl)phenylcarbamateYield 60.3%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirred solution of 2-(4-aminophenyl)propane-1,2,3-triol (900 mg, 4.918 mmol, 1.0 eq) in THF/H2O/sat. NaHCO3 (4 mL: 2 mL: 4 mL) was added phenyl chloroformate (0.68 mL, 5.367 mmol, 1.1 eq) at 0° C. and the mixture was stirred at RT for 0.5 h, then the THF was evaporated, the residue was diluted with EtOAc (20 mL), washed with water (20 mL) followed by brine and the solvent evaporated. The resulting residue was purified by CC using MeOH/CHCl3 (1:19) as eluent to get phenyl 4-(1,2,3-trihydroxypropan-2-yl)phenylcarbamate (900 mg, 60%, white solid; TLC system: MeOH/CHCl3 (1:9), Rf: 0.4).

Workup

  1. customthe THF was evaporated
  2. additionthe residue was diluted with EtOAc (20 mL)
  3. washwashed with water (20 mL)
  4. customthe solvent evaporated
  5. customThe resulting residue was purified by CC

Sources & evidence

ORD record
ord-bf5be4af1429467ba9eaf2f06b17a11c
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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