Acetic Acid → 4-{2-[(2-tert-Butoxycarbonyl-ethyl)-(3-chloro-4-trifluoromethoxy-phenyl)-amino]-ethylamino}-butyric acid methyl ester

HRID 2095519Notes

Reaction equation

HRID 2095519 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][CH2:8][N:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[C:15]([Cl:24])[CH:14]=1)[CH2:10][CH:11]=O)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32].C(N(CC)CC)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:34][O:33][C:31](=[O:32])[CH2:30][CH2:29][CH2:28][NH:27][CH2:11][CH2:10][N:9]([CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:25])[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:21])([F:23])[F:22])=[C:15]([Cl:24])[CH:14]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 27563834-Aminobutyric acid methyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 866526903-[(3-Chloro-4-trifluoromethoxy-phenyl)-(2-oxo-ethyl)-amino]-propionic acid tert-butyl ester

Product 1

HCID 670743024-{2-[(2-tert-Butoxycarbonyl-ethyl)-(3-chloro-4-trifluoromethoxy-phenyl)-amino]-ethylamino}-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.50 g (1.3 mmol) of 3-[(3-chloro-4-trifluoromethoxy-phenyl)-(2-oxo-ethyl)-amino]-propionic acid tert-butyl ester in 6 ml dichloromethane was added dropewise to a cooled (0° C., pH ca. 5) suspension of 0.22 g (1.4 mmol) methyl 4-aminobutyrate hydrochloride, 0.18 ml (1.3 mmol) triethylamine, 0.15 ml (2.6 mmol) acetic acid and 0.32 g (1.5 mmol) sodium triacetoxyborohydride in 4 ml of dichloromethane and stirred 30 min at 0° C. The reaction was extracted with aqueous saturated NaHCO3/EtOAc (3×). The organic phases were washed with aqueous saturated NaHCO3 and dried over Na2SO4 to yield after evaporation of the solvent 0.61 g (83%) of the titled compound as yellow oil. MS: 483.19 (MH+, Cl).

Workup

  1. temperaturea cooled
  2. extractionThe reaction was extracted with aqueous saturated NaHCO3/EtOAc (3×)
  3. washThe organic phases were washed with aqueous saturated NaHCO3
  4. dry with materialdried over Na2SO4
  5. customto yield
  6. customafter evaporation of the solvent 0.61 g (83%) of the titled compound as yellow oil

Sources & evidence

ORD record
ord-be1559557b7e463ea95ac63924b8a4e8
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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