Glycine tert-butyl ester hydrochloride → HCID 178444050, compound

HRID 923587Notes

Reaction equation

HRID 923587 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([CH:23]=O)=[CH:22][C:16]=3[N:15]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Cl.[NH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].[Na]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([CH2:23][NH:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:22][C:16]=3[N:15]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 2725036Glycine tert-butyl ester hydrochlorideHCID 5360545SodiumHCID 178444053HCID 178444053, compound

Product 1

HCID 178444050HCID 178444050, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-(heptyloxy)benzyl)-1H-benzo[d]imidazole-5-carbaldehyde INT-47 (571 mg, 1.63 mmol) in DCM (6 mL) was added tert-butyl 2-aminoacetate hydrochloride (328 mg, 1.96 mmol). After 1 h, sodium triacetoxyhydroborate (691 mg, 3.26 mmol) was added. After stirring at room temperature for 18 h, the reaction mixture was quenched with NaHCO3 (10 mL), stirred for 10 min and split through a hydrophobic frit and evaporated. The crude product was purified by column chromatography (MeOH/EA) to give 228 mg (30%) of tert-butyl 2-(((2-(4-(heptyloxy)benzyl)-1H-benzo[d]imidazol-5-yl)methyl)amino)acetate INT-48 as a pale yellow oil. LCMS-ESI (m/z) calculated for C28H39N3O3: 465; found 466 [M+H]+, tR=1.17 min (Method 3).

Workup

  1. customthe reaction mixture was quenched with NaHCO3 (10 mL)
  2. stirringstirred for 10 min
  3. customsplit through a hydrophobic frit
  4. customevaporated
  5. customThe crude product was purified by column chromatography (MeOH/EA)

Sources & evidence

ORD record
ord-22bb30a5a7f543f9a609ef93ca626e88
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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