Benzyl chloroformate → Ammonia

HRID 901621Notes

Reaction equation

HRID 901621 reaction equation
[CH3:1][N:2]([CH3:36])[C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=1)[CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:18][C@@H:19]([C:21]1[CH:32]=[CH:31][C:24]2[O:25][C:26]([CH3:30])([CH3:29])[O:27][CH2:28][C:23]=2[CH:22]=1)[OH:20].C(N(C(C)C)CC)(C)C.Cl[C:47]([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:48].C(=O)(O)[O-].[Na+]>ClCCl>[NH3:2].[CH3:36][N:2]([CH3:1])[C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=1)[CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:18][C@@H:19]([C:21]1[CH:32]=[CH:31][C:24]2[O:25][C:26]([CH3:29])([CH3:30])[O:27][CH2:28][C:23]=2[CH:22]=1)[OH:20])[C:47](=[O:48])[O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

7

Reactant 4

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 66846385HCID 66846385, compound

Product 2

HCID 222AmmoniaHCID 66845304HCID 66845304, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1R)-2-{[6-(2-{[3-(dimethylamino)benzyl]oxy}ethoxy)hexyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (200 mg) in dichloromethane (10 ml) was treated under nitrogen with diisopropylethylamine (0.09 ml) followed by benzyl chloroformate (0.099 ml) and the mixture was stirred at 20° for 4 h. Saturated sodium bicarbonate solution was added and the mixture extracted with dichloromethane. The extract was dried (Na2SO4) and the solvent evaporated in vacuo. The residue was purified by SPE (silica, 10 g). Elution with dichloromethane—ethanol—0.880 ammonia (250:8:1) gave the title compound (220 mg). LCMS RT=3.87 min.

Workup

  1. extractionthe mixture extracted with dichloromethane
  2. dry with materialThe extract was dried (Na2SO4)
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by SPE (silica, 10 g)
  5. washElution with dichloromethane—ethanol—0

Sources & evidence

ORD record
ord-cf98ecb0ec4f440c9b76b32acf86b389
Source dataset
uspto-grants-2008_04
Patent number
US07361787B2

Reaction notes

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