Acetic Acid → Ethyl[(2-{(tert-butoxycarbonyl)[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}ethyl)amino]acetate

HRID 1466059Notes

Reaction equation

HRID 1466059 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][CH2:12][N:13]([CH2:21][CH:22]=O)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:10][C:5]=2[CH2:4][O:3]1.Cl.[NH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][NH:25][CH2:22][CH2:21][N:13]([C:14]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:20])[CH2:12][CH2:11][C:9]1[CH:8]=[CH:7][C:6]2[C:2](=[O:1])[O:3][CH2:4][C:5]=2[CH:10]=1)[CH3:31]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 117599267tert-Butyl[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl](2-oxoethyl)carbamate

Product 1

HCID 131732682Ethyl[(2-{(tert-butoxycarbonyl)[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}ethyl)amino]acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-Butyl [2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl](2-oxoethyl)carbamate (580 mg, 1.8 mmol) in MeOH (50 mL) was added ethyl aminoacetate hydrochloride (380 mg, 2.7 mmol), sodium cyanoborohydride (340 mg, 5.4 mmol) and a drop of acetic acid. The reaction was allowed to stir at RT for 16 hours. LC showed the desired product, which was purified by silica gel chromatography. LC-MS (IE, m/z): 407 [M+1]+.

Sources & evidence

ORD record
ord-2cdad6736174498ba5a23da25df394b2
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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