Triethylamine → HCID 22258085, compound

HRID 1610996Notes

Reaction equation

HRID 1610996 reaction equation
[C:1]([NH:4][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:10]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:32])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].C(N(CC)CC)C.C1C=NC2N(O)N=NC=2C=1.[CH3:50][O:51]CC(O)=O.CCN=C=NCCCN(C)C>C(Cl)Cl.CCOC(C)=O>[Cl:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:24][C:10]1[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:12][CH:13]=[CH:14][C:9]=1[CH:5]([NH:4][C:1](=[O:3])[CH2:2][O:51][CH3:50])[C:6]([OH:8])=[O:7]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 12251Methoxyacetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 10151939HCID 10151939, compound

Product 1

HCID 22258085HCID 22258085, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Example 13 Part A compound (222 mg, 0.45 mmol) under argon at room temperature in CH2Cl2 (1.5 mL) was added triethylamine (85 μL, 0.6 mmol), HOAt (69 mg, 0.5 mmol) and methoxyacetic acid (46 mg, 0.5 mmol) was added EDAC (96 mg, 0.5 mmol). After 16 h, the reaction mixture was diluted with EtOAc, washed once with 10% citric acid, dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel provided the title compound as a colorless oil, 153 mg (74% yield). LC/MS gave the correct molecular ion [(M+H)+=518] for the desired compound.

Workup

  1. washwashed once with 10% citric acid
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-3b5d2821f5b9414ab1e372ee4a16f240
Source dataset
uspto-grants-2006_01
Patent number
US06984645B2

Reaction notes

Loading…