Water → Benzyl (2,2-dimethoxyethyl)carbamate

HRID 898730Notes

Reaction equation

HRID 898730 reaction equation
[CH2:1]([O:8][C:9]([O:11]N1C(=O)CCC1=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][CH:21]([O:24][CH3:25])[CH2:22][NH2:23].C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[CH3:19][O:20][CH:21]([O:24][CH3:25])[CH2:22][NH:23][C:9](=[O:11])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 83172Benzyl succinimido carbonate2×HCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 10800009Benzyl (2,2-dimethoxyethyl)carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
5 °C

Procedure

N-(Benzyloxycarbonyloxy)succinimide (74.5 Kg) was charged to a 200-gallon reactor, followed by toluene (235.1 Kg). The mixture was stirred for 15 minutes and cooled to 5° C. A solution of aminoacetaldehyde dimethylacetal (30 Kg) and triethylamine (28.9 Kg) in toluene (26.1 Kg) was charged slowly to the reactor over a 1 hour period while maintaining the internal temperature below 30° C. The mixture was stirred at 20° C. until there remained no more than 1.0% CbzOSu, as determined by HPLC. Water (150 Kg) was charged to the reactor and the contents of the reactor were stirred for 15 minutes. The layers were separated and the organic layer was washed with 5% ammonium chloride (2×151 Kg) followed by a water wash (150 Kg). The product was taken onto the next step as a solution, without isolation.

Workup

  1. temperaturewhile maintaining the internal temperature below 30° C
  2. stirringThe mixture was stirred at 20° C. until there
  3. stirringthe contents of the reactor were stirred for 15 minutes
  4. customThe layers were separated
  5. washthe organic layer was washed with 5% ammonium chloride (2×151 Kg)
  6. washwash (150 Kg)

Sources & evidence

ORD record
ord-d21615c455144e55a9c38498635fc59a
Source dataset
uspto-grants-2008_04
Patent number
US07351833B2

Reaction notes

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