Hydrochloric Acid → benzyl (2,2-dimethoxyethyl)carbamate

HRID 575860Notes

Reaction equation

HRID 575860 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][CH:9]([O:13][CH3:14])[CH2:10][NH:11][CH3:12].CC1OCCC1.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].Cl>O>[CH2:25]([O:24][C:22](=[O:23])[N:11]([CH2:10][CH:9]([O:13][CH3:14])[O:8][CH3:7])[CH3:12])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 73012-MethyltetrahydrofuranHCID 85032,2-DimethoxyethylmethylamineHCID 10387Benzyl chloroformateHCID 11430Potassium Carbonate

Product 1

HCID 58058121benzyl (2,2-dimethoxyethyl)carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

K2CO3 (8.4 kg, 60 mol, 1.8 eq.) and H2O (49.3 kg, 2.6 volumes) were placed in the reaction vessel and stirred. N-methylaminoacetaldehyde dimethylacetal (6.5 kg, 54 mol, 1.6 eq) and MeTHF (20.2 kg, 2.9 volumes) were added. The resulting mixture was cooled to 5° C. Benzyl chloroformate (6.8 kg, 37.6 mol, 1.1 eq.) was added over a period of about 30 minutes, while maintaining the temperature below 10° C. The feed line was rinsed with MeTHF (4.3 kg). The mixture was then maintained at 5° C. and stirred for 1 hour. The layers were separated and the organic layer was washed with 1N HCl (14.3 kg, 11.7 mol, 1.4 volumes) and used directly in the next step.

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. washThe feed line was rinsed with MeTHF (4.3 kg)
  3. temperatureThe mixture was then maintained at 5° C.
  4. stirringstirred for 1 hour
  5. customThe layers were separated

Sources & evidence

ORD record
ord-35fcaaa4c62640618cf285485b910565
Source dataset
uspto-grants-2015_05
Patent number
US09035061B2

Reaction notes

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