Dichloromethane → Ammonia

HRID 916060Notes

Reaction equation

HRID 916060 reaction equation
[Si]([O:8][C@H:9]([C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[C:38]([CH2:43][OH:44])[CH:37]=1)[CH2:10][NH:11][C@H:12]([CH3:35])[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][CH:29]=[CH:28][C:27]=2[O:32][CH2:33][CH3:34])=[O:23])[CH:17]=[CH:18][CH:19]=1)(C(C)(C)C)(C)C.CO.O.ClCCl>CO>[NH3:11].[CH2:33]([O:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[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:36]2[CH:41]=[CH:40][C:39]([OH:42])=[C:38]([CH2:43][OH:44])[CH:37]=2)[CH3:35])[CH:15]=1)[CH3:34]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 22242641Methanol--water (1/1)HCID 68976436HCID 68976436, compound

Product 2

HCID 222AmmoniaHCID 11318122HCID 11318122, 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-(2-ethoxybenzyl)propanamide (Preparation 47) 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-f0b4d028d8a8443280eeb9ea42e152f3
Source dataset
uspto-grants-2007_09
Patent number
US07268147B2

Reaction notes

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