Ethanolamine → HCID 69195690, compound

HRID 132128Notes

Reaction equation

HRID 132128 reaction equation
[CH3:1][CH:2]([CH3:18])[CH2:3][C@H:4]([NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=1)[C:5]([OH:7])=O.[CH2:19]([CH2:21][NH2:22])[OH:20].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[OH:20][CH2:19][CH2:21][NH:22][C:5]([C@@H:4]([NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=1)[CH2:3][CH:2]([CH3:1])[CH3:18])=[O:7]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 42255868HCID 42255868, compound

Product 1

HCID 69195690HCID 69195690, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-4-Methyl-2-(3-methyl-benzoylamino)-pentanoic acid (1 g. 4.0 mmol), ethanolamine (270 mg, 4.4 mmol) and HOBt (596 mg, 4.4 mmol) were treated with DCM (20 mL) followed by EDCI (845 mg, 4.4 mmol). The reaction was allowed to stir for 2 h and then purified directly by silica gel column chromatography using ethyl acetate and hexane to afford the product (350 mg, 30%) as a solid: 1H NMR (CDCl3, 400 MHz) δ 0.89-0.99 (m, 6H), 1.67-1.79 (m, 3H), 2.37 (s, 3H), 3.31-3.41 (m, 1H), 3.42-3.52 (m, 1H), 3.61 (dd, 1H, J1=2.7, J2=8.1), 7.24-7.34 (m, 2H), 7.43 (dd, 1H, J1=J2=5.3), 7.57-7.63 (m, 2H); HPLC-MS calcd. for C16H24N2O3 (M+H+) 292.18, found 292.2.

Workup

  1. custompurified directly by silica gel column chromatography

Sources & evidence

ORD record
ord-1e4d79f9969d4a82a59fa863d9850152
Source dataset
uspto-grants-2008_06
Patent number
US07384970B2

Reaction notes

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