Acetic Acid → HCID 89545047, compound

HRID 2283439Notes

Reaction equation

HRID 2283439 reaction equation
[C:1]([C:9]1[C:10]([F:18])=[C:11]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH:12]=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:20]([O:22][C:23](=[O:28])[CH2:24][C@@H:25]([NH2:27])[CH3:26])[CH3:21].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClC(Cl)C>[CH2:20]([O:22][C:23](=[O:28])[CH2:24][C@@H:25]([NH:27][CH2:12][C:11]1[CH:14]=[CH:15][C:16]([Cl:17])=[C:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]=1[F:18])[CH3:26])[CH3:21]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 42614517Butanoic acid, 3-aMino-, ethyl ester, hydrochloride, (3S)-HCID 89544754HCID 89544754, compound2×

Product 1

HCID 89545047HCID 89545047, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Step 1 To a solution of 3-benzoyl-4-chloro-2-fluoro-benzaldehyde (Intermediate 10, 337 mg, 1.29 mmol) in dichloroethane (5 ml) was sequentially added (S)-3-amino-butyric acid ethyl ester hydrochloride (237 mg, 1.41 mmol), triethylamine (0.196 ml, 1.41 mmol), sodium triacetoxyborohydride (818 mg, 3.86 mmol) and glacial acetic acid (0.159 ml 2.57 mmol). The mixture was stirred for 2 days then dilute sodium bicarbonate was added. After stirring for 10 minutes, the mixture was extracted with ethyl acetate. The organic liquors were washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by silica chromatography eluting with 20-100% ethyl acetate/petroleum ether furnishing (3S)-3-(3-benzoyl-4-chloro-2-fluoro-benzylamino)-butyric acid ethyl ester as a colourless oil (203 mg). MS: [M+H] 378

Workup

  1. stirringAfter stirring for 10 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic liquors were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica chromatography
  7. washeluting with 20-100% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-a0064b92e7794a21989a6ec430afecfc
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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