Triethylamine → HCID 57871407, compound

HRID 550224Notes

Reaction equation

HRID 550224 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(CC)CC.[CH2:36]([C:38]([C:58]1[CH:59]=[C:60]2[C:65](=[CH:66][CH:67]=1)[CH:64]=[C:63]([C:68](O)=[O:69])[CH:62]=[CH:61]2)([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH:48]([CH2:55][CH3:56])[CH:49]([OH:54])[C:50]([CH3:53])([CH3:52])[CH3:51])=[C:43]([CH3:57])[CH:42]=1)[CH2:39][CH3:40])[CH3:37]>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][C:68]([C:63]1[CH:62]=[CH:61][C:60]2[C:65](=[CH:66][CH:67]=[C:58]([C:38]([CH2:36][CH3:37])([C:41]3[CH:46]=[CH:45][C:44]([O:47][CH:48]([CH2:55][CH3:56])[CH:49]([OH:54])[C:50]([CH3:51])([CH3:52])[CH3:53])=[C:43]([CH3:57])[CH:42]=3)[CH2:39][CH3:40])[CH:59]=2)[CH:64]=1)=[O:69]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 122755Glycine methyl ester hydrochlorideHCID 57871421HCID 57871421, compound

Product 1

HCID 57871407HCID 57871407, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add glycine methyl ester hydrochloride (95 mg, 0.755 mmol), HOBT (102 mg, 0.755 mmol), EDCI (206 mg, 1.08 mmol), and Et3N (0.4 ml, 0.726 mmol) to diastereomeric isomer pair 1 of 6-{1-ethyl-1-[4-(1-ethyl-2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-naphthalene-2-carboxylic acid (343 mg, 0.72 mmol) and CH2Cl2 (5 ml). Stir the reaction for 14 h. Concentrate the reaction mixture in vacuo, and chromatograph the residue (CH2Cl2 to 15% EtOAc/CH2Cl2) to give the title compound as a colorless foam (373 mg, 95%). 1NMR (400 MHz, CDCl3) δ ppm: 0.64 (t, J=7.6 Hz, 6H), 0.93 (t, J=8.4 Hz, 3H), 0.93 (s, 9H), 1.68 (m, 1H), 1.81 (m, 1H), 2.12 (s, 3H), 2.18 (q, 4H), 2.60 (bs, 1H), 3.27 (s, 1H), 3.83 (s, 3H), 4.27 (dd, J=5.6, 3.2 Hz, 1H), 4.31 (d, J=5.2 Hz, 2H), 6.63 (d, J=8.0 Hz, 1H), 6.75 (t, J=4.8 Hz, 1H), 6.89 (d, J=2.4 Hz, 1H), 6.93 (dd, J=6.4, 2.0 Hz, 1H), 7.18 (dd, J=6.8, 2.0 Hz, 1H), 7.75 (d, J=8.4 Hz, 1H), 7.83 (d, J=2.0, 1H), 7.86 (m, 2H), 8.26 (s, 1H). High Res. ES-MS: 570.3116; calc. for C34H45NO5+Na: 570.3196.

Workup

  1. customthe reaction for 14 h
  2. concentrationConcentrate the reaction mixture in vacuo, and chromatograph the residue (CH2Cl2 to 15% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-96b54e3b2c48448eab5a2a85c17997a6
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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