(3R,4R)-3-[1-(2-sulfamoylamino-ethyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester → (3R,4R)-N-[2-[7-[4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl]-3,4-dihydro-2H-quinolin-1-yl]-ethyl]-sulfamide

HRID 1531515Notes

Reaction equation

HRID 1531515 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[CH:16][CH:15]=2)[C@@H:10]([O:34][CH2:35][C:36]2[CH:45]=[C:44]3[C:39]([CH2:40][CH2:41][CH2:42][N:43]3[CH2:46][CH2:47][NH:48][S:49](=[O:52])(=[O:51])[NH2:50])=[CH:38][CH:37]=2)[CH2:9]1)=O)(C)(C)C>ClCCCl.[Br-].[Zn+2].[Br-]>[CH3:33][O:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:24][CH2:23][CH2:22][CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C@H:11]2[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]2[O:34][CH2:35][C:36]2[CH:45]=[C:44]3[C:39]([CH2:40][CH2:41][CH2:42][N:43]3[CH2:46][CH2:47][NH:48][S:49]([NH2:50])(=[O:51])=[O:52])=[CH:38][CH:37]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 69489189(3R,4R)-3-[1-(2-sulfamoylamino-ethyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 57052509(3R,4R)-N-[2-[7-[4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl]-3,4-dihydro-2H-quinolin-1-yl]-ethyl]-sulfamide

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

In analogy to the procedure described in example 1(e), the (3R,4R)-3-[1-(2-sulfamoylamino-ethyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester was deprotected with zinc bromide in 1,2-dichloroethane to yield the (3R,4R)-N-[2-[7-[4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl]-3,4-dihydro-2H-quinolin-1-yl]-ethyl]-sulfamide as a yellow oil; MS: 639 (M+H)+.

Sources & evidence

ORD record
ord-1fd676f79a8548b785998cb04b3e19e6
Source dataset
uspto-grants-2001_03
Patent number
US06197959B1

Reaction notes

Loading…