Dichloromethane → Ammonia

HRID 916063Notes

Reaction equation

HRID 916063 reaction equation
[Si]([O:8][C@H:9]([C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([CH2:42][OH:43])[CH:36]=1)[CH2:10][NH:11][C@H:12]([CH3:34])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][C:22]([N:24]2[CH2:33][CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25]2)=[O:23])[CH:15]=1)(C(C)(C)C)(C)C.CO.O.ClCCl>CO>[NH3:11].[CH2:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:32][CH2:33][N:24]1[C:22](=[O:23])[CH2:21][CH2:20][C:16]1[CH:15]=[C:14]([CH2:13][C@H:12]([NH:11][CH2:10][C@@H:9]([C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([CH2:42][OH:43])[CH:36]=2)[OH:8])[CH3:34])[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 22242641Methanol--water (1/1)HCID 68977722HCID 68977722, compound

Product 2

HCID 222AmmoniaHCID 11340768HCID 11340768, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared from 4-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[((1R)-2-{3-[3-(3,4-dihydroisoquinolin-2-(1H)-yl)-3-oxopropyl]phenyl}-1-methylethyl)amino]ethyl}-2-(hydroxymethyl)phenol (Preparation 50) according to the method for example 1 using methanol:water (2.4:1 v/v) instead of acetic acid as solvent and using dichloromethane:methanol: 880 ammonia (95:5:0.5 by volume) as the column eluent to give the title compound as a white solid.

Sources & evidence

ORD record
ord-e3eb96dd20604de181c5418f92f51b38
Source dataset
uspto-grants-2007_09
Patent number
US07268147B2

Reaction notes

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