Triethylamine → 3-(4-Benzyloxy-benzoylamino)-propionic acid methyl ester

HRID 1669222Notes

Reaction equation

HRID 1669222 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:19][O:20][C:21](=[O:25])[CH2:22][CH2:23][NH2:24].C(N(CC)CC)C.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:19][O:20][C:21](=[O:25])[CH2:22][CH2:23][NH:24][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 738804-(Benzyloxy)benzoic acidHCID 2734767Methyl 3-aminopropanoate hydrochloride

Product 1

HCID 266353683-(4-Benzyloxy-benzoylamino)-propionic acid methyl esterYield 92.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-benzyloxybenzoic acid (8.92 g, 39.08 mmol) and 3-amino-propionic acid methyl ester hydrochloride (6.00 g, 42.98 mmol) in CH2Cl2 (100 mL) was added DMAP (catalytic), triethylamine (6.60 mL, 47.35 mmol), and EDCI (9.00 g, 46.94 mmol). The mixture was stirred at RT for 12 h. The mixture was diluted with CH2Cl2. The organics were washed with 1N HCl, 2N NaOH, water, and brine (1×100 mL each), and dried with MgSO4 to yield 11.28 g (92%) of the title compound.

Workup

  1. washThe organics were washed with 1N HCl, 2N NaOH, water, and brine (1×100 mL each)
  2. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-74926c26f41f46d1b5bfbc364f15b45c
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

Loading…