Monomethyl terephthalate → HCID 59006939, compound

HRID 1174537Notes

Reaction equation

HRID 1174537 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1.C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH2:47]([O:49][C:50]1[CH:51]=[C:52]([C@@H:58]2[C@H:63]([NH2:64])[CH2:62][CH2:61][O:60][CH2:59]2)[CH:53]=[CH:54][C:55]=1[O:56][CH3:57])[CH3:48]>ClCCl>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:64][C@@H:63]2[CH2:62][CH2:61][O:60][CH2:59][C@@H:58]2[C:52]2[CH:53]=[CH:54][C:55]([O:56][CH3:57])=[C:50]([O:49][CH2:47][CH3:48])[CH:51]=2)=[O:10])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 15513Monomethyl terephthalateHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59006942HCID 59006942, compound

Product 1

HCID 59006939HCID 59006939, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1 mmol of terephthalic acid monomethyl ester, 5 mmol of ethyl di-isopropylamine and 1.1 mmol of O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluoro-phosphate (HBTU) in 20 ml of dichloromethane is stirred for 30 min at RT. After addition of 1.1 mmol of (3R,4R)-3-(3-ethoxy-4-methoxy-phenyl)-tetrahydro-pyran-4-ylamine the suspension is stirred over night at RT. The mixture is concentrated under reduced pressure and the solid residue is purified by column chromatography on SiO2 (dichloromethane/ethyl acetate 85/15 vol/vol), the main product fraction is separated and concentrated yielding the title compound as grayish solid residue. M.p. 166-167.5° C.

Workup

  1. stirringis stirred over night at RT
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customthe solid residue is purified by column chromatography on SiO2 (dichloromethane/ethyl acetate 85/15 vol/vol)
  4. customthe main product fraction is separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-31a7bcc9040a44fd8e7b54050c6242a5
Source dataset
uspto-grants-2010_11
Patent number
US07838521B2

Reaction notes

Loading…