Dichloromethane → Ammonia

HRID 916062Notes

Reaction equation

HRID 916062 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][CH:25]2[CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:23])[CH:17]=[CH:18][CH:19]=1)(C(C)(C)C)(C)C.CO.O.ClCCl>CO>[NH3:11].[CH2:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:33][CH:25]1[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 58959815HCID 58959815, compound

Product 2

HCID 222AmmoniaHCID 11306347HCID 11306347, 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-(2,3-dihydro-1H-inden-2-yl)propanamide (Preparation 49) 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-ddceeb27cc194a04a0b2c49eedc83977
Source dataset
uspto-grants-2007_09
Patent number
US07268147B2

Reaction notes

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