Diisopropylethylamine → HCID 69819698, compound

HRID 1006322Notes

Reaction equation

HRID 1006322 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[ClH:15].[CH3:16][O:17][C:18](=[O:21])[CH2:19][NH2:20].C(N(CC)C(C)C)(C)C.[CH3:31][O:32][C:33]1[CH:40]=[CH:39][C:38]([O:41][C:42]([F:45])([F:44])[F:43])=[CH:37][C:34]=1[CH:35]=O>ClCCl.C(O)(=O)C>[ClH:15].[CH3:16][O:17][C:18](=[O:21])[CH2:19][NH:20][CH2:35][C:34]1[CH:37]=[C:38]([O:41][C:42]([F:43])([F:44])[F:45])[CH:39]=[CH:40][C:33]=1[O:32][CH3:31]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 27833642-Methoxy-5-(trifluoromethoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 69819698HCID 69819698, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (5.6 g) was added portionwise to a mixture of glycine methyl ester hydrochloride (1.63 g), N,N-diisopropylethylamine (2.27 ml) and 2-methoxy-5-(trifluoromethoxy)benzaldehyde (3.8 g) in a mixture of dichloromethane (30 ml) and acetic acid (3 drops) at 0° C. and the whole was stirred at 5° C.˜room temperature overnight. The mixture was partitioned between ethyl acetate and 2N sodium hydroxide. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (2:1). The fractions containing the objective compound were collected and evaporated under reduced pressure and treated with 4N hydrogen chloride in ethyl acetate solution to give N-[2-methoxy-5-(trifluoromethoxy)benzyl]glycine methyl ester hydrochloride (2.76 g) as a colorless powder.

Workup

  1. customThe mixture was partitioned between ethyl acetate and 2N sodium hydroxide
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (2:1)
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure
  10. additiontreated with 4N hydrogen chloride in ethyl acetate solution

Sources & evidence

ORD record
ord-888e9e5f5d3e4a6f897ebb2348d773a8
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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