Dicyclohexylcarbodiimide → cis-3-(3-Methoxyphenoxy)-6-(2-quinolyl)methoxy-4-chromanyl N,N-Dimethylglycinate

HRID 346024

Reaction equation

HRID 346024 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=1)[O:6][C@H:7]1[C@@H:16]([OH:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)[CH:14]=2)[O:9][CH2:8]1.Cl.[CH3:34][N:35]([CH3:40])[CH2:36][C:37](O)=[O:38].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:34][N:35]([CH3:40])[CH2:36][C:37]([O:17][C@H:16]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)[CH:14]=2)[O:9][CH2:8][C@H:7]1[O:6][C:5]1[CH:30]=[CH:31][CH:32]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:38]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 75605N,N-Dimethylglycine hydrochlorideHCID 86745187(+/-)-cis-3-(3-Methoxyphenoxy)-6-(2-quinolyl)methoxy-4-chromanol

Product 1

HCID 67592358cis-3-(3-Methoxyphenoxy)-6-(2-quinolyl)methoxy-4-chromanyl N,N-Dimethylglycinate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the title product of Example 26 (0.493 g), 4-(dimethylamino)pyridine (0.226 g) and N,N-dimethylglycine hydrochloride (0.193 g) in 30 ml of CH2Cl2 was added a solution of dicyclohexylcarbodiimide in 5 ml of CH2Cl2. After stirring 18 hours, by-product dicyclohexyl urea was recovered by filtration and the filtrate stripped to an oily solid which was chromatographed on a silica gel column with ether as eluant to yield purified title product, 0.44 g. 1H-NMR(CDCl3)delta(ppm): 2.15 (s, 6H), 3.15 (s, 2H), 3.80 (s, 3H), 4.30 (d, J=5Hz, 2H), 4.90 (m, 1H), 6.30 (d, J=3, 1H), 6.30-8.30 (m, 13H).

Workup

  1. filtrationby-product dicyclohexyl urea was recovered by filtration
  2. customwas chromatographed on a silica gel column with ether as eluant
  3. customto yield
  4. custompurified title product, 0.44 g

Sources & evidence

ORD record
ord-287602f428a5480abfc0bad1b5de47a5
Source dataset
uspto-grants-1991_10
Patent number
US05059609

Linked notes

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