Triethylamine → HCID 178491487, compound

HRID 133794Notes

Reaction equation

HRID 133794 reaction equation
[OH:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=O.[C:15]([NH:18][C:19]1[C:36]([Cl:37])=[CH:35][C:22]([CH2:23][NH:24]/[C:25](/[NH2:34])=[N:26]\[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:21][C:20]=1[Cl:38])(=[O:17])[CH3:16].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl>[C:15]([NH:18][C:19]1[C:20]([Cl:38])=[CH:21][C:22]([CH2:23][NH:24]/[C:25](=[N:26]\[C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:32])[CH3:30])/[NH:34][C:4](=[O:6])[CH2:3][CH:2]([OH:1])[C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[CH:35][C:36]=1[Cl:37])(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 149273073-Hydroxy-3-(4-methoxyphenyl)propanoic acidHCID 178474312HCID 178474312, compound

Product 1

HCID 178491487HCID 178491487, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-hydroxy-3-(4-methoxyphenyl)propanoic acid (13.7 mg, 0.07 mmol), (Z)-tert-butyl (4-acetamido-3,5-dichlorobenzylamino)(amino)-methylenecarbamate (26.3 mg), PyBop (36.4 mg), and triethylamine (0.01 mL) in dichloromethane (0.35 mL) was stirred at room temperature for 12 h. The crude reaction mixture was purified directly by preparative TLC eluting with 30% ethyl acetate/70% hexanes to give the title compound as a clear sticky oil (30 mg, 77% yield). 1H NMR (400 MHz, CDCl3) δ 1.48 (m, 9 H) 2.21 (s, 3 H) 2.70 (m, 2 H) 3.78 (m, 3 H) 4.55 (m, 2 H) 4.95 (m, 1 H) 6.80-7.00 (m, 3 H) 7.24-7.38 (m, 4 H), 9.10 (m, 1 H), 12.30 (m, 1 H). HPLC retention time: 2.493 min (method A). MS (ESI) (M+H)+ 553.08.

Workup

  1. customThe crude reaction mixture
  2. customwas purified directly by preparative TLC
  3. washeluting with 30% ethyl acetate/70% hexanes

Sources & evidence

ORD record
ord-e2bed52f21754bca906fd61d26a1a75a
Source dataset
uspto-grants-2008_06
Patent number
US07390925B2

Reaction notes

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