Acetic Acid → ethyl N-{4-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzyl}glycinate

HRID 2281073Notes

Reaction equation

HRID 2281073 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.Cl.[NH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:13][CH2:14]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH:16]=[CH:17][C:18]([CH2:19][NH:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 867119874-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzaldehyde

Product 1

HCID 70978183ethyl N-{4-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzyl}glycinate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzaldehyde (68 mg, 0.22 mmol) was dissolved in 1,2-dichloroethane (2.2 mL) and treated with ethyl aminoacetate hydrochloride (34 mg, 0.28 mmol) and acetic acid (25 uL, 0.44 mmol). The solution was stirred at ambient temperatures for 30 minutes and treated with sodium triacetoxyborohydride (51 mg, 0.24 mmol). The mixture was stirred at ambient temperature until complete, diluted with ethyl acetate (50 mL) and washed with sodium bicarbonate (2×30 mL, aqueous saturated). The organic extract was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (100:0 to 97:3; dichloromethane:methanol) to afford the titled compound as a clear oil.

Workup

  1. stirringThe mixture was stirred at ambient temperature until complete,
  2. washwashed with sodium bicarbonate (2×30 mL, aqueous saturated)
  3. extractionThe organic extract
  4. dry with materialwas dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (100:0 to 97:3; dichloromethane:methanol)

Sources & evidence

ORD record
ord-77141b3d74094ce0857ed44f50520dd9
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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