Dichloromethane → Ammonia

HRID 916061Notes

Reaction equation

HRID 916061 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:15]=[C:16]([CH2:20][CH2:21][C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([CH3:33])[CH:27]=2)=[O:23])[CH:17]=[CH:18][CH:19]=1)(C(C)(C)C)(C)C.CO.O.ClCCl>CO>[NH3:11].[CH3:33][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][C:29]=1[CH3:32])[CH2:25][NH:24][C:22](=[O:23])[CH2:21][CH2:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([CH2:13][C@H:12]([NH:11][CH2:10][C@H:9]([OH:8])[C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([CH2:42][OH:43])[CH:36]=2)[CH3:34])[CH:15]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 22242641Methanol--water (1/1)HCID 58959771HCID 58959771, compound

Product 2

HCID 222AmmoniaHCID 11271807HCID 11271807, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared from 3-{3-[(2R)-2-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]phenyl}-N-(3,4-dimethylbenzyl)propanamide (Preparation 48) 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 (94:6:0.6 by volume) as the column eluent to give the title compound as a white solid.

Sources & evidence

ORD record
ord-cc575db8321f4a198e6dd60ef715a7e4
Source dataset
uspto-grants-2007_09
Patent number
US07268147B2

Reaction notes

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