Acetic Acid → HCID 21073106, compound

HRID 1373210Notes

Reaction equation

HRID 1373210 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[NH2:23])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Si:25]([O:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].C(O)(=O)C.C([BH3-])#N.[Na+]>O.CO>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[NH:23][CH2:37][C:36]2[CH:35]=[CH:34][C:33]([O:32][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[CH:40][CH:39]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehydeHCID 21072922HCID 21072922, compound

Product 1

HCID 21073106HCID 21073106, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of tert-butyl[3-(2-amino-5-chlorophenoxy)benzyl]carbamate (3.48 g, 10 mmols), 4-tert-butyldimethylsilyloxybenzaldehyde (2.19 g, 12 mmols), acetic acid (1 ml) and methanol (40 ml) was stirred at room temperature for 1 hour, to which was added sodium cyanoborohydride (0.75 g, 12 mmols). Next, this was stirred at room temperature for 3 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed with water, then dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography to give an oil of tert-butyl[3-[2-(4-tert-butyldimethylsilyloxybenzylamino)-5-chlorophenoxy]benzyl]carbamate (2.40 g, 42.4%).

Workup

  1. stirringNext, this was stirred at room temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-311b4d5f17f04088abebdc64af0d9f66
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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