Methyl chloroformate → HCID 131728963, compound

HRID 2428138Notes

Reaction equation

HRID 2428138 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[C:6]([SiH2:10][O:11][C:12]([CH3:23])([CH3:22])[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:16][NH2:17])([CH3:9])([CH3:8])[CH3:7].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:5][O:4][C:2](=[O:3])[NH:17][CH2:16][C:15]1[CH:18]=[CH:19][C:20]([Cl:21])=[C:13]([C:12]([CH3:23])([CH3:22])[O:11][SiH2:10][C:6]([CH3:9])([CH3:8])[CH3:7])[CH:14]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 1373299203-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzylamine

Product 1

HCID 131728963HCID 131728963, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl chloroformate (1.98 mL, 25.2 mmol) was added to a sol. of 3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzylamine (6.00 g, 20.9 mmol) and DIPEA (7.33 mL, 42.0 mmol) in CH2Cl2 (100 mL) at rt. The mixture was stirred for 1 h at rt, and more CH2Cl2 was added. The mixture was washed with aq. sat. NH4Cl, aq. 1M NaOH, and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 1:5) yielded the title compound (5.39 g, 75%). LC-MS: tR=1.02 min; ES+: 344.38.

Workup

  1. washThe mixture was washed with aq. sat. NH4Cl, aq. 1M NaOH, and brine
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the crude by FC (EtOAc/heptane 1:5)

Sources & evidence

ORD record
ord-195ce7b844d045e0baa08e207ac246b0
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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